3149-28-8

Basic information

• Product Name: 2-Methoxypyrazine
• Synonyms: 2-METHOXYPYRAZINE;METHOXYPYRAZINE;METHOXYPYRAZINE, 2-;FEMA 3302;FEMA NUMBER 3302;methoxy-pyrazin;2-METHOXYPYRAZINE 99+% FCC;2-Methoxypyrazine,98%
• CAS NO: 3149-28-8
• Molecular Formula: C₅H₆N₂O
• Molecular Weight: 110.11
• EINECS: 221-579-8
• Product Categories: Pyrazine;Pyrazines;Alkoxypyrazines;pyrazine Flavor;Building Blocks;Heterocyclic Building Blocks;Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 3149-28-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 60-61 °C29 mm Hg(lit.)
• Flash Point: 114 °F
• Appearance: /
• Density: 1.14 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.24mmHg at 25°C
• Refractive Index: n20/D 1.509(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 0.53±0.10(Predicted)
• BRN: 2241
• CAS DataBase Reference: 2-Methoxypyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxypyrazine(3149-28-8)
• EPA Substance Registry System: 2-Methoxypyrazine(3149-28-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-22-37/38-41
• Safety Statements: 16-26-39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 3149-28-8(Hazardous Substances Data)

Usage

Description

2-Methoxypyrazine is a pyrazine derivative that is known for its distinctive kernels and cocoa-like aroma. It is a commonly used flavoring agent in the food industry and can be found in various forms such as 3-Isobutyl-2-methoxypyrazine, 3-sec-butyl-2-methoxypyrazine, 3-alkyl-2-methoxypyrazines, and 3-isopropyl-2-methoxypyrazine. These derivatives are also present in wine and various fruits such as berries and grapes. It is present at ultra-trace levels in sauvignon blanc and cabernet sauvignon grapes and wine, contributing a unique aroma even at low parts per trillion levels. Additionally, it has been reported to be found in cooked beef, cocoa, malt, and krill.

Uses

Used in Flavoring Industry:
2-Methoxypyrazine is used as a flavoring agent for its sweet, nutty, and cocoa-like odor. It is particularly valued for its ability to contribute a distinctive "green, capsicum (bell pepper), herbaceous, and earthy" aroma that is characteristic of certain wines, such as sauvignon blanc and cabernet sauvignon.
Used in Wine Industry:
2-Methoxypyrazine is used as a flavoring agent in the wine industry to enhance the aroma of sauvignon blanc and cabernet sauvignon wines. Its presence at ultra-trace levels contributes to the unique and characteristic aroma of these wines.
Used in Food Industry:
2-Methoxypyrazine is used as a flavoring agent in the food industry to impart a sweet, nutty, and cocoa-like aroma to various food products. Its derivatives can also be found in various fruits, such as berries and grapes, adding to their distinct flavor profiles.
Used in Aroma Research:
2-Methoxypyrazine is used in aroma research due to its low odor threshold of 700 ppb in water. This property makes it an important compound for studying the sensory properties of various foods and beverages, as well as for developing new flavoring agents and additives.

References

Murray, K. E., J. Shipton, and F. B. Whitfield. "2-methoxypyrazines and the flavour of green peas (Pisum sativum). " Chemistry & Industry 27.14(1970):897-898. Hashizume, Katsumi, and Takashi Samuta. "Grape maturity and light exposure affect berry methoxypyrazine concentration." American Journal of Enology and Viticulture 50.2 (1999): 194-198. Hartmann, Peter J., Harold M. McNair, and Bruce W. Zoecklein. "Measurement of 3-alkyl-2-methoxypyrazine by headspace solid-phase microextraction in spiked model wines." American Journal of Enology and Viticulture 53.4 (2002): 285-288. HASHiZUME, Katsumi, and Norihiko Umeda. "Methoxypyrazine content of Japanese red wines." Bioscience, biotechnology, and biochemistry 60.5 (1996): 802-805. Lacey, Michael J., et al. "Methoxypyrazines in Sauvignon blanc grapes and wines." American Journal of Enology and Viticulture 42.2 (1991): 103-108.

Preparation

From 2-hydroxypyrazine by various routes.

Safety Profile

Skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C5H6N2O/c1-8-5-4-6-2-3-7-5/h2-4H,1H3

Upstream product

• 14508-49-7 2-chloropyrazin 
• 124-41-4 sodium methylate 
• 23902-69-4 3-methoxypyrazine 1-oxide 
• 32046-05-2 2-methoxypyrazine 1-oxide 
• 865-33-8 potassium methanolate 
• 6542-37-6 (1s,5s)-5-hydroxymethyl-3,7-dioxa-1-azabicyclo[3.3.0]octane 

Downstream Products

• 135085-57-3 (2-methoxypyrazinyl)phenylmethanone 
• 1080-87-1 α-(2-pyrazinyl)phenylacetonitrile 
• 91392-53-9 (2-methoxypyrazinyl)phenylmethanol 
• 2847-30-5 2-methoxy-3-methylpyrazine 
• 13134-34-4 N-phenylpyrazin-2-ylamine 
• 63874-90-8 3-methoxypyrazine-2-carbaldehyde 
• 1385043-49-1 1-(3-methoxy-1-trifluoromethanesulfonyl-1,2-dihydropyrazin-2-yl)cyclohexane-1-carboxylic acid 
• 1385043-51-5 methyl 1-(3-oxo-1,4-bis(trifluoromethanesulfonyl)-1,2,3,4-tetrahydropyrazin-2-yl)-cyclohexane-1-carboxylate 
• 1385043-50-4 methyl 1-(3-methoxy-1-trifluoromethanesulfonyl-1,2-dihydropyrazin-2-yl)cyclohexane-1-carboxylate 
• 1372607-34-5 1-cyclohexanecarbonyl-3-methoxy-1,2-dihydropyrazine 
• 1372607-35-6 1-phenoxycarbonyl-3-methoxy-1,2-dihydropyrazine 
• 1372607-31-2 1-benzyloxycarbonyl-3-methoxy-1,2-dihydropyrazine 
• 1372607-33-4 1-phenylcarbonyl-3-methoxy-1,2-dihydropyrazine 
• 99984-63-1 2-methoxy-3-phenylpyrazine 

Relevant articles and documents

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.

α-(3,7-Dioxa-r-1-azabicyclo[3.3.0]oct-c-5-ylmethoxy)-diazines. Part 1: Synthesis and stereochemistry. Extension to s-triazine series

The general and efficient synthesis of the title compounds, consisting of the (selective) replacement of chlorine in commercial α-chlorodiazines and cyanuryl chloride by the 3,7-dioxa-r-1-azabicyclo[3.3.0]oct-c-5-ylmethoxy group (Williamson method) is described. The stereochemistry of this new series of derivatives is analysed in terms of different conformational chirality exhibited in solution (1H NMR) versus solid state (X-ray diffractometry), meso against chiral forms, respectively. In solid state, the inclusion capacity of some chiral networks as well as their supramolecular aggregation is pointed out. A good correlation between rotameric behaviour of the c-5-di(s-tri)diazinyloxymethyl group in the two states is found.

Studies on Pyrazines. Part 10. Substitution Effect on Reaction of Pyrazine N-Oxides with Phosphoryl chloride

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