15707-34-3

Basic information

• Product Name: 2,3-Dimethyl-5-ethylpyrazine
• Synonyms: 2-ethyl-5,6-dimethylpyrazine;6-Ethyl-2,3-dimethylpyrazine;Pyrazine, 6-ethyl-2,3-dimethyl;2,3-DIMETHYL-5-ETHYLPYRAZINE;5-ETHYL-2,3-DIMETHYLPYRAZINE;2,3-dimethyl-6-ethylpyrazine;ethyldimethylpyrazine,2,3-dimethyl-6-ethylpyrazine,6-ethyl-2,3-dimethylpyrazine;2,3-DIMETHYL-5-ETHYL PYRAZINE FEMA NO.--------
• CAS NO: 15707-34-3
• Molecular Formula: C₈H₁₂N₂
• Molecular Weight: 136.19
• Product Categories: Pyrazine
• Mol File: 15707-34-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 76°C/15mmHg(lit.)
• Flash Point: 70.8 °C
• Appearance: /
• Density: 0.964 g/cm³
• Vapor Pressure: 0.74mmHg at 25°C
• Refractive Index: 1.4990 to 1.5030
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 2.61±0.10(Predicted)
• CAS DataBase Reference: 2,3-Dimethyl-5-ethylpyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethyl-5-ethylpyrazine(15707-34-3)
• EPA Substance Registry System: 2,3-Dimethyl-5-ethylpyrazine(15707-34-3)

Safety Data

• Hazardous Substances Data: 15707-34-3(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
2,3-Dimethyl-5-ethylpyrazine is used as a flavoring agent for imparting a roasted or nutty taste and aroma to food products. Its natural occurrence and distinctive scent profile make it a popular choice in enhancing the flavor profiles of various consumables.
Used in Food Products:
2,3-Dimethyl-5-ethylpyrazine is used as a flavor enhancer in food products for adding depth and complexity to their taste, particularly in products that aim to replicate the flavor of roasted or nutty ingredients.
Used in Tobacco and Chocolate Flavors:
In the tobacco industry, 2,3-Dimethyl-5-ethylpyrazine is used as a flavoring agent to create a more nuanced and appealing smoking experience. Similarly, in the chocolate industry, it is used to enhance the richness and complexity of chocolate flavors, contributing to a more satisfying taste.
Used in Pharmaceuticals:
2,3-Dimethyl-5-ethylpyrazine has been studied for its potential applications in the pharmaceutical sector, although the specific uses are not detailed in the provided materials. Its exploration in this field suggests that it may have therapeutic properties or serve as a precursor in the synthesis of pharmaceutical compounds.
Used as a Synthetic Intermediate in Organic Chemistry:
2,3-Dimethyl-5-ethylpyrazine also serves as a synthetic intermediate in organic chemistry, indicating its utility in the synthesis of more complex organic molecules, potentially for various industrial applications beyond the flavor and fragrance sector.

InChI:InChI=1/C8H12N2/c1-4-8-5-9-6(2)7(3)10-8/h5H,4H2,1-3H3

Upstream product

• 56-45-1 L-serin 
• 50-81-7 ascorbic acid 
• 72-19-5 L-threonine 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 65464-21-3 2,3-dimethyl-1,4-diazine N-oxide 
• 5910-89-4 2,3-dimethylpyrazine 
• 123-38-6 propionaldehyde 
• 5051-06-9 (S)-6-Amino-2-((S)-2-amino-propionylamino)-hexanoic acid 
• 78-98-8 2-oxopropanal 
• 997-62-6 Gly-L-Lys-OH 
• 56-87-1 L-lysine 
• 56-40-6 glycine 
• 492-62-6 alpha-D-glucopyranose 
• 556-50-3 glycylglycine 

Relevant articles and documents

Method for site-selective alkylation of Diazine-N-oxide using phosphonium ylides

- N - Oxide (Diazine -)N-The position selective Oxides-C alkylation of H) relates to a method alkylation. To the present invention, a plurality of diazine compounds can be alkylated by selectively introducing an alkyl group to a diazine compound known as a core unit structure in a medicine, and synthesis of a plurality of diazine compounds (varenicline) paenibacillin A, which is a natural product, can be synthesized.

Site-Selective C-H Alkylation of Diazine N-Oxides Enabled by Phosphonium Ylides

The synthesis of alkylated diazine derivatives is important for their practical utilization as pharmaceuticals and for other purposes. Herein, we describe the metal-free site-selective C-H alkylation of diazine N-oxides using phosphonium ylides that affords a variety of alkylated diazine derivatives with broad functional group tolerance. The utility of this method is showcased by the late-stage functionalization of a commercially available drug such as varenicline. Notably, the sequential C-H alkylation of pyrazine N-oxides for the total synthesis of a pyrazine-containing natural product, paenibacillin A, highlights the importance of this method.

Alkylations and hydroxymethylations of pyrazines via green minisci-type reactions

A new general methodology utilizing Minisci-type chemistry has been developed that cleanly and efficiently prepares alkyl- and (hydroxymethyl) pyrazines. The new methods eliminate toxic catalysts and halogenated solvents, providing a greatly improved route to these natural products which are prevalent in many natural systems as bacterial volatiles, plant volatiles, and insect pheromones.

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.

Regioselective synthesis of trialkylpyrazines via nickel-catalyzed Negishi cross-coupling of pyrazine triflate

A regioselective synthesis of trialkylpyrazines via nickel-catalyzed cross-coupling reaction of pyrazine triflate is reported. The 5-substituted 2,3-dimethylpyrazine derivatives including trail pheromone components of the ant Eutetramorium mocquerysi have been successfully synthesized in good yields by nickel-catalyzed Negishi cross-coupling reactions of pyrazine triflate mediated by alkyl and arylzinc halides. Georg Thieme Verlag Stuttgart · New York.

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.

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

Regioselective Synthesis of Alkylpyrazines

A new, regioselective synthesis of alkylpyrazines begins with condensation of α-oximido carbonyl compounds with allylamines.The resulting imines are isomerized in the presence of potassium tert-butoxide to the corresponding 1-hydroxy-1,4-diazahexatrienes.Thermal electrocyclization-aromatization to pyrazines is best performed after O-acylation of the oximes with methyl chloroformate.