13360-64-0

Basic information

• Product Name: 2-Ethyl-5-methylpyrazine
• Synonyms: ethylmethylpyrazine,2-ethyl-5-methylpyrazine;Pyrazine, 2-ethyl-5-methyl-;5-ETHYL-2-METHYLPYRAZINE;2-Ethyl-5-methylpyrazine;2-Methyl-5-ethylpyrazine;2-Methyl-5-ethylpirazine;2-ethyl-5-Methyl pyraine;2-Methyl-5-ethyl pyraine
• CAS NO: 13360-64-0
• Molecular Formula: C₇H₁₀N₂
• Molecular Weight: 122.17
• EINECS: 236-416-6
• Product Categories: Pyrazines;pyrazine Flavor
• Mol File: 13360-64-0.mol

Chemical Properties

• Boiling Point: 170.8 °C at 760 mmHg
• Flash Point: 63 °C
• Appearance: /
• Density: 0.977 g/cm³
• Vapor Pressure: 1.92mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.94±0.10(Predicted)
• CAS DataBase Reference: 2-Ethyl-5-methylpyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethyl-5-methylpyrazine(13360-64-0)
• EPA Substance Registry System: 2-Ethyl-5-methylpyrazine(13360-64-0)

Safety Data

• Hazardous Substances Data: 13360-64-0(Hazardous Substances Data)

Usage

Uses

Used in Food and Beverage Industry:
2-Ethyl-5-methylpyrazine is used as a flavor enhancer for its nutty, roasted, and grassy odor. It is added to various food and beverage products to improve their overall taste and aroma, making it more appealing to consumers.
Used in Coffee Aroma:
2-Ethyl-5-methylpyrazine is used as a flavoring agent in the coffee industry, contributing to the rich and complex aroma of the beverage. Its addition helps to create a more enjoyable coffee experience for consumers.
Used in Roasted Barley:
In the production of roasted barley, 2-Ethyl-5-methylpyrazine is used as a flavor enhancer. It adds a nutty and roasted aroma to the barley, enhancing its overall taste and making it more palatable.
Used in Dairy Products:
2-Ethyl-5-methylpyrazine is used as an additive in the dairy industry to improve the flavor and aroma of various dairy products, such as milk, cheese, and yogurt.
Used in Peanuts and Nut Products:
The compound is used as a flavor enhancer in peanuts and other nut products, adding a nutty and roasted aroma that complements the natural taste of these products.
Used in Popcorn:
2-Ethyl-5-methylpyrazine is used in the popcorn industry to enhance the flavor and aroma of the snack, making it more enjoyable for consumers.
Used in Potato and Soy Products:
In the production of potato and soy products, 2-Ethyl-5-methylpyrazine is used as a flavor enhancer, adding a nutty and roasted aroma to these products.
Used in Smoked Fish:
The compound is used in the smoked fish industry to enhance the flavor and aroma of the fish, making it more appealing to consumers.
Used in Bread:
2-Ethyl-5-methylpyrazine is used as a flavor enhancer in the production of wheat and rye bread, adding a nutty and roasted aroma to the bread.
Used in Asparagus:
In the preparation of asparagus, 2-Ethyl-5-methylpyrazine is used as a flavor enhancer, adding a nutty and roasted aroma to the vegetable.
Used in Bell Pepper:
The compound is used in the bell pepper industry to enhance the flavor and aroma of the pepper, making it more enjoyable for consumers.
Used in Roasted Coconut:
2-Ethyl-5-methylpyrazine is used as a flavor enhancer in the roasted coconut industry, adding a nutty and roasted aroma to the coconut.
Used in Cooked Beef:
In the preparation of cooked beef, the compound is used as a flavor enhancer, adding a nutty and roasted aroma to the meat.
Used in Beer:
2-Ethyl-5-methylpyrazine is used in the beer industry to enhance the flavor and aroma of the beverage, making it more enjoyable for consumers.
Used in Whiskey:
The compound is used as a flavor enhancer in the whiskey industry, adding a nutty and roasted aroma to the spirit.
Used in Cocoa:
2-Ethyl-5-methylpyrazine is used in the cocoa industry to enhance the flavor and aroma of chocolate products, making them more appealing to consumers.
Used in Tea:
The compound is used as a flavor enhancer in the tea industry, adding a nutty and roasted aroma to the beverage.
Used in Cooked Shrimp:
In the preparation of cooked shrimp, 2-Ethyl-5-methylpyrazine is used as a flavor enhancer, adding a nutty and roasted aroma to the seafood.

Preparation

By alkylation of dimethyl-2,5-pyrazine.

InChI:InChI=1/C7H10N2/c1-3-7-5-8-6(2)4-9-7/h4-5H,3H2,1-2H3

Upstream product

• 2280-44-6 D-Glucose 
• 56-41-7 L-alanin 
• 50-99-7 D-glucose 
• 410538-35-1 LysAla*hydrobromide 
• 103404-72-4 LysLeu*acetate 
• 275366-32-0 LysSer*hydrochloride 
• 106325-92-2 Lys-Cys 
• 56-87-1 L-lysine 
• 56-45-1 L-serin 
• 61-90-5 L-leucine 
• 56-86-0 L-glutamic acid 
• 63-91-2 L-phenylalanine 
• 56-40-6 glycine 
• 45234-02-4 Lys-Glu 

Downstream Products

• 91920-66-0 2-(1-Bromo-ethyl)-5-methyl-pyrazine 

Relevant articles and documents

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.

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.

The effect of pH on the formation of aroma compounds produced by heating a model system containing l-ascorbic acid with l-threonine/l-serine

The identification of aroma compounds, formed from the reactions of l-ascorbic acid with l-threonine/l-serine at five different pH values (5.00, 6.00, 7.00, 8.00, or 9.55) and 143 ± 2 °C for 2 h, was performed using a SPME-GC-MS technique, and further use

Formation of pyrazines in maillard model systems of lysine-containing dipeptides

Whereas most studies concerning the Maillard reaction have focused on free amino acids, little information is available on the impact of peptides and proteins on this important reaction in food chemistry. Therefore, the formation of flavor compounds from the model reactions of glucose, methylglyoxal, or glyoxal with eight dipeptides with lysine at the N-terminus was studied in comparison with the corresponding free amino acids by means of stir bar sorptive extraction (SBSE) followed by GC-MS analysis. The reaction mixtures of the dipeptides containing glucose, methylglyoxal, and glyoxal produced 27, 18, and 2 different pyrazines, respectively. Generally, the pyrazines were produced more in the case of dipeptides as compared to free amino acids. For reactions with glucose and methylglyoxal, this difference was mainly caused by the large amounts of 2,5(6)-dimethylpyrazine and trimethylpyrazine produced from the reactions with dipeptides. For reactions with glyoxal, the difference in pyrazine production was rather small and mostly unsubstituted pyrazine was formed. A reaction mechanism for pyrazine formation from dipeptides was proposed and evaluated. This study clearly illustrates the capability of peptides to produce flavor compounds that can differ from those obtained from the corresponding reactions with free amino acids.

Mechanisms of Formation of Alkylpyrazines in the Maillard Reaction

The formation of alkylpyrazines was investigated in the reaction of glucose and fructose with -alanine and glycine.The reaction systems were heated for 7 min at 180 deg C.GC-MS and GC-MS/MS data were used to determine the rate of incorporati