13925-00-3

Basic information

• Product Name: Ethylpyrazine
• Synonyms: ethyl-pyrazin;FEMA NUMBER 3281;FEMA 3281;ETHYLPYRAZINE;ETHYLPYRAZINE, 2-;2-ETHYLPYRAZINE;2-ethyl-1,4-diazine;2-ETHYLPYRAZINE 98+%
• CAS NO: 13925-00-3
• Molecular Formula: C₆H₈N₂
• Molecular Weight: 108.14
• EINECS: 237-691-5
• Product Categories: Pyrazines;Mono- & Polyalkylpyrazines;pyrazine Flavor;Building Blocks;Heterocyclic Building Blocks
• Mol File: 13925-00-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 155 °C
• Boiling Point: 152-153 °C(lit.)
• Flash Point: 109 °F
• Appearance: clear colorless to yellow liquid
• Density: 0.984 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.01mmHg at 25°C
• Refractive Index: n20/D 1.498(lit.)
• Storage Temp.: Flammables area
• Solubility: freely soluble
• PKA: 1.62±0.10(Predicted)
• Water Solubility: freely soluble
• BRN: 108200
• CAS DataBase Reference: Ethylpyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: Ethylpyrazine(13925-00-3)
• EPA Substance Registry System: Ethylpyrazine(13925-00-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 10-41-37/38-22
• Safety Statements: 16-39-26
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: UQ3330000
• TSCA: T
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 13925-00-3(Hazardous Substances Data)

Usage

Description

Ethylpyrazine, also known as 2-Ethylpyrazine, is a volatile aroma compound that belongs to the class of pyrazines. It is characterized by its musty, nutty, buttery, and peanut-like odor, and a chocolate-peanut taste. Ethylpyrazine is mainly formed in food products such as roasted coffee beans or roasted sesame seeds due to the Maillard reaction between sugars and proteins during the roasting process. It is found in various food items, including bakery products, cocoa products, coffee, meat, peanuts, filberts, potato products, beer, whiskey, tea, soybeans, rice, roasted coconut, corn tortillas, shrimp, crayfish, asparagus, boiled beef, malt whiskey, and malt.
Ethylpyrazine is a clear colorless to yellow liquid with a peanut butter, musty, nutty, woody, and peanut buttery odor. It has a taste threshold value of 10 ppm and an aroma threshold value of 4 to 22 ppm. At 1.0% concentration, it exhibits aroma characteristics of nutty, musky, fermented, coffee, roasted, cocoa, and meaty nuances.

Uses

1. Used in Pharmaceutical Synthesis:
Ethylpyrazine is used as a reagent in the synthetic preparation of various pharmaceutical goods. It has been screened for potential activities as an H1-antihistamine, which can be beneficial in the development of medications for treating allergic reactions.
2. Used in the Synthesis of Pyrazinoic Acid:
Ethylpyrazine has been utilized in the synthesis of pyrazinoic acid, which is an important compound in the pharmaceutical industry.
3. Used in Flavor and Fragrance Industry:
Due to its distinct aroma and taste characteristics, Ethylpyrazine is used in the flavor and fragrance industry to enhance the sensory properties of various products, such as food and beverages.
4. Used in Food Industry:
Ethylpyrazine is naturally found in a wide range of food products, contributing to their unique taste and aroma. It is used in the food industry to improve the flavor profile of various dishes and beverages.

Preparation

By alkylation of methylpyrazine with methyliodide.

InChI:InChI=1/C6H8N2/c1-2-6-5-7-3-4-8-6/h3-5H,2H2,1H3

Upstream product

• 13961-37-0 2-ethylpiperazine 
• 110-85-0 piperazine 
• 123-84-2 N-(2-hydroxypropyl)ethylenediamine 
• 107-15-3 ethylenediamine 
• 56-45-1 L-serin 
• 56-41-7 L-alanin 
• 56-87-1 L-lysine 
• 131543-46-9 Glyoxal 
• 50-81-7 ascorbic acid 
• 72-19-5 L-threonine 
• 492-62-6 alpha-D-glucopyranose 
• 56-40-6 glycine 
• 50-99-7 D-glucose 
• 59-51-8 DL-methionine 

Downstream Products

• 98-97-5 2-pyrazylcarboxylic acid 
• 91920-65-9 2-(1'-bromoethyl)pyrazine 
• 94777-52-3 2-(1-hydroxyethyl)pyrazine 
• 98-96-4 pyrazinamide 
• 6164-79-0 methyl pyrazine-2-carboxylate 
• 13961-37-0 2-ethylpiperazine 
• 83227-47-8 4'-chloro-2-(2-pyrazinyl)-propiophenone 
• 83227-48-9 2',4'-dichloro-2-(2-pyrazinyl)-propiophenone 
• 867035-87-8 dimethyl-{2-[3-(1-pyrazin-2-yl-ethyl)-1H-inden-2-yl]-ethyl}-amine 
• 1201762-98-2 C₆H₁₀N₃⁽¹⁺⁾*C₉H₁₁O₃S^(1-) 
• 1201762-89-1 C₆H₁₀N₃⁽¹⁺⁾*C₉H₁₁O₃S^(1-) 
• 22047-25-2 acetylpyrazine 

Relevant articles and documents

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Comparison of pyrazines formation in methionine/glucose and corresponding Amadori rearrangement product model

The generation of pyrazines in a binary methionine/glucose (Met/Glc) mixture and corresponding methionine/glucose-derived Amadori rearrangement product (MG-ARP) was studied. Quantitative analyses of pyrazines and methional revealed that MG-ARP generated more methional compared to Met/Glc, whereas lower content and fewer species of pyrazines were observed in the MG-ARP model. Comparing the availability of α-dicarbonyl compounds generated from the Met/Glc model, methylglyoxal (MGO) was a considerably effective α-dicarbonyl compound for the formation of pyrazines during MG-ARP degradation, but glyoxal (GO) produced from MG-ARP did not effectively participate in the corresponding formation of pyrazines due to the asynchrony on the formation of GO and recovered Met. Diacetyl (DA) content was not high enough to form corresponding pyrazines in the MG-ARP model. The insufficient interaction of precursors and rapid drops in pH limited the formation of pyrazines during MG-ARP degradation. Increasing reaction temperature could reduce the negative inhibitory effect by promoting the content of precursors.

Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents

The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

Impact of the N-terminal amino acid on the formation of pyrazines from peptides in maillard model systems

Only a minor part of Maillard reaction studies in the literature focused on the reaction between carbohydrates and peptides. Therefore, in continuation of a previous study in which the influence of the peptide C-terminal amino acid was investigated, this study focused on the influence of the peptide N-terminal amino acid on the production of pyrazines in model reactions of glucose, methylglyoxal, or glyoxal. Nine different dipeptides and three tripeptides were selected. It was shown that the structure of the N-terminal amino acid is determinative for the overall pyrazine production. Especially, the production of 2,5(6)-dimethylpyrazine and trimethylpyrazine was low in the case of proline, valine, or leucine at the N-terminus, whereas it was very high for glycine, alanine, or serine. In contrast to the alkyl-substituted pyrazines, unsubstituted pyrazine was always produced more in the case of experiments with free amino acids. It is clear that different mechanisms must be responsible for this observation. This study clearly illustrates the capability of peptides to produce flavor compounds such as pyrazines.