2-methoxy-6-methylpyrazine Chemical Properties

Boiling point:

48-50 °C(Press: 15 Torr)

Density 

1.068±0.06 g/cm3(Predicted)

FEMA 

3183 | 2,5 OR 6-METHOXY-3-METHYLPYRAZINE (MIXTURE OF ISOMERS)

pka

1.32±0.10(Predicted)

Odor

at 0.10 % in propylene glycol. roasted hazelnut almond peanut

Odor Type

nutty

JECFA Number

788

LogP

1.21

EPA Substance Registry System

Pyrazine, 2-methoxy-6-methyl- (2882-21-5)

2-methoxy-6-methylpyrazine Usage And Synthesis

Chemical Properties

2 or 5 or 6-Methoxy-3-methylpyrazine has an aroma reminiscent of hazelnut, almond and peanut. The methyl methoxy pyrazines are used as nut-like flavoring agents for foods and beverages. The 2-methoxy-3-methyl derivative is used as a coffee aroma enhancing agent.

Occurrence

Reported found in sherry and krill.

Uses

2-Methoxy-6-methylpyrazine can be used for drug storage package storing antiviral and antibacterial.

Definition

ChEBI: 2-Methoxy-6-methylpyrazine is a member of pyrazines and an aromatic ether.

Preparation

From 2-methylpyrazine by various routes.

Aroma threshold values

Detection: 3 to 7 ppb

Synthesis

General procedure for the synthesis of 2-methoxy-6-methylpyrazine from 2-chloro-6-methylpyrazine: 2-chloro-6-methylpyrazine (24 g, 186.7 mmol) was suspended in anhydrous methanol (240 mL) under the protection of nitrogen followed by the addition of sodium methanolate (12.1 g, 224 mmol). The reaction mixture was stirred at 60-70°C for 16 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered to remove insoluble material. The filtrate was concentrated under reduced pressure to give 2-methoxy-6-methylpyrazine (22 g, 95% yield). The product was characterized by 1H NMR (CDCl3, 400 MHz): δ 7.98 (s, 1H), 7.94 (s, 1H), 3.91 (s, 3H), 3.40 (s, 3H). LC-MS analysis showed a retention time tR = 1.47 min (Method 14) and a mass-to-charge ratio of m/z = 124.8 [M + H]+.

References

[1] Patent: WO2016/174188, 2016, A1. Location in patent: Page/Page column 47; 48

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