24683-00-9

Basic information

• Product Name: 2-Methoxy-3-isobutyl pyrazine
• Synonyms: 2-methoxy-3-(2-methyl-propyl) pyrazine;2-methoxy-3-(2-methylpropyl)-pyrazin;2-methoxy-3-(2-methylpropyl)-Pyrazine;3-methoxy-2-isobutylpyrazine;Pyrazine, 2-(2-methylpropyl)-3-methoxy;Pyrazine, 2-isobutyl-3-methoxy;Pyrazine, 2-methoxy-3-(2-methylpropyl)-;Pyrazine, 3-methoxy-2-(2-methylpropyl)
• CAS NO: 24683-00-9
• Molecular Formula: C₉H₁₄N₂O
• Molecular Weight: 166.22
• EINECS: 246-402-1
• Product Categories: Pyrazines;Pyrazine;Heterocyclic Compounds;Alkoxypyrazines;Mono- & Polyalkylpyrazines;pyrazine Flavor;500 Series Drinking Water Methods;Drinking WaterEPA;Odor Standards;Chromatography;Environmental Standards;Alphabetical Listings;Flavors and Fragrances;I-L;Building Blocks;Heterocyclic Building Blocks
• Mol File: 24683-00-9.mol

Chemical Properties

• Boiling Point: 294.44°C (rough estimate)
• Flash Point: 176 °F
• Appearance: Clear colorless/Liquid
• Density: 0.99 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.49(lit.)
• Storage Temp.: 2-8°C
• PKA: 0.80±0.10(Predicted)
• CAS DataBase Reference: 2-Methoxy-3-isobutyl pyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxy-3-isobutyl pyrazine(24683-00-9)
• EPA Substance Registry System: 2-Methoxy-3-isobutyl pyrazine(24683-00-9)

Safety Data

• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-36-24/25-45-36/37-16-7
• RIDADR: UN 1230 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 24683-00-9(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
2-Methoxy-3-isobutyl pyrazine is used as a flavoring agent for its characteristic green bell pepper and green pea odor. It is added to various food products to enhance their flavor and aroma.
Used in Agricultural Industry:
2-Methoxy-3-isobutyl pyrazine is used as a natural odorant in the agricultural industry, particularly in the cultivation of crops that are known for their bell pepper or green pea aroma.
Used in Chemical Research:
2-Methoxy-3-isobutyl pyrazine is used as a model odorant molecule in electrochemical assays for the detection of odorant molecules based on a rat odorant-binding protein (rOBP3). This application aids in understanding the interaction between odorant molecules and olfactory receptors, which is crucial for the development of new odorant detection technologies.
Used in Synthesis:
2-Methoxy-3-isobutyl pyrazine can be synthesized by condensation of leucine amide with glyoxal, followed by methylation with CH2H2. This synthesis method is useful for producing the compound in a controlled laboratory setting for various applications, including research and commercial purposes.

Preparation

By condensation of leucine amide with glyoxal followed by methylation with CH2H2

InChI:InChI=1/C9H14N2O/c1-7(2)6-8-9(12-3)11-5-4-10-8/h4-5,7H,6H2,1-3H3

Upstream product

• 25680-53-9 2-hydroxy-3-isobutyl-pyrazine 
• 74-88-4 methyl iodide 
• 124-41-4 sodium methylate 
• 57674-17-6 3-sec-butyl-2-chloropyrazine 
• 67-56-1 methanol 

Relevant articles and documents

New approach to asymmetrically substituted methoxypyrazines, derivatives of wine flavors

An original synthetic route to asymmetrically substituted methoxypyrazine (MP) derivatives is described. The first step of the synthesis is achieved by condensation of 1,2-aminoalcohols with Boc-protected aliphatic aminoacids followed by cycloimine formation and aromatization via chlorination. Introduction of methoxy group was then achieved by alkoxy-de-halogenation. The use of primary or secondary aminopropanol enabled the direct and selective introduction of methyl group, in 5- or 6-position, which can be easily functionalized. Aromatization of diketopiperazine, prepared from l-valine and l-glutamic acid dimethyl ester, made possible a direct introduction of a functionalized alkyl chain. These reactions are also suitable for the synthesis of naturally-occurring MPs such as wine flavor components and biologically active substances.

1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents

The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and 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) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

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.

New insights into the synthesis and characterization of 2-methoxy-3-alkylpyrazines and their deuterated isotopologues

A previously described synthetic route for preparation of 2-methoxy-3-alkylprazines (MPs) based on condensation of glyoxal with an α-amino acid amide, followed by methylation with iodomethane yields 3-alkyl-1-methyl-1H-pyrazin-2-ones (N-methyl derivatives), rather than the designated 2-methoxy-3-alkylpyrazines (O-methyl derivatives). Despite similar nuclear magnetic resonance and mass spectral properties, gas chromatographic (GC) retention indices differ significantly, indicating chemical difference. With the example of 3-sec-butyl-1-methyl-1H-pyrazin-2-one and its 3-sec-butyl-1-[2H3]methyl-1H-pyrazin-2-one isotopologue, the position of the methyl group introduced could be assigned unambiguously, using heteronuclear multiple bond correlation (HMBC) NMR experiments. For future characterization, the spectroscopic (NMR, EI+MS) as well as GC retention index data on two stationary phases of the most aroma relevant MPs and their deuterated isotopologues are summarized. Copyright

Preparation of labelled 2-methoxy-3-alkylpyrazines: Synthesis and characterization of deuterated 2-methoxy-3-isopropylyrazine and 2-methoxy-3-isobutylpyrazine

Efficient synthetic routes for a number of deuterated analogues of 2-methoxy-3-isopropylpyrazines and 2-methoxy-3-isobutylpyrazines have been developed involving the condensation of glyoxal with an α-amino acid amide followed by methylation with iodomethane. In this way [2H3]2-methoxy-3-isopropylpyrazine, 2-methoxy-3-isopropyl-[2H2]pyrazine, [2H3]2-methoxy-3-isopropyl- [2H2]pyrazine, [2H3]2-methoxy-3-isobutylpyrazine; 2-methoxy-3-isobutyl-[2H2]pyrazine and [2H3]2-methoxy-3-isobutyl- [2H2]pyrazine were prepared and characterized by NMR and MS. Copyright