2-Methoxypyrazine Chemical Properties

Boiling point:

60-61 °C/29 mmHg (lit.)

Density 

1.14 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.509(lit.)

FEMA 

3302 | METHOXYPYRAZINE

Flash point:

114 °F

storage temp. 

Sealed in dry,Room Temperature

pka

0.53±0.10(Predicted)

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

1.140

Odor

at 1.00 % in dipropylene glycol. sweet nutty cocoa

Odor Type

chocolate

JECFA Number

787

BRN 

2241

LogP

0.75

CAS DataBase Reference

3149-28-8(CAS DataBase Reference)

NIST Chemistry Reference

Pyrazine, methoxy-(3149-28-8)

EPA Substance Registry System

Pyrazine, methoxy- (3149-28-8)

Safety Information

Hazard Codes 

Xn

Risk 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

HS Code 

29339990

MSDS

• Language:English Provider:2-Methoxypyrazine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Methoxypyrazine Usage And Synthesis

Description

2-methoxypyrazine is a kind of pyrazine derivative. It emits a kernels and cocoa-like aroma. It is a commonly used daily, food flavoring agent. It has many kinds of flavoring derivatives such as 3-Isobutyl-2-methoxypyrazine, 3-sec-butyl-2-methoxypyrazine, 3-alkyl-2-methoxypyrazines and 3-isopropyl-2-methoxypyrazine. There derivatives could be found in wine and many kinds of fruits such as berry and grapes.

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.

Description

Methoxypyrazine has an odor threshold of 700 ppb in water. Methoxypyrazine may be prepared from 2-hydroxypyrazine by various routes.

Chemical Properties

Methoxypyrazine has a sweet, nutty, cocoa odor. Methoxypyrazine contributes a distinctive “green, capsicum (bell pepper), herbaceous and earthy” aroma that is quite characteristic of certain wines, such as sauvignon blanc and cabernet sauvignon.

Chemical Properties

Colorless liquid

Occurrence

Present at ultra-trace levels in sauvignon blanc and cabernet sauvignon grapes and wine. Methoxypyrazine contributes a distinctive wine aroma, even at low parts per trillion levels. Also reported found in cooked beef, cocoa, malt and krill.

Definition

ChEBI: Methoxypyrazine is an aromatic ether and a member of pyrazines.

Preparation

From 2-hydroxypyrazine by various routes.

Aroma threshold values

700 ppb in water

Safety Profile

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

2-Methoxypyrazine(3149-28-8)Related Product Information

• Sulfachoropyrazine sodium
• Tetramethylpyrazine
• 2-Methylpyrazine
• Pyrazinamide
• Glipizide
• 2-Methoxy-3-isobutyl pyrazine
• 2-Isopropyl-5-methoxypyrazine,2-Isopropyl-6-methoxypyrazine,2-Isopropyl-3-methoxypyrazine
• 2-METHYL-6-PROPOXYPYRAZINE
• 2-ETHYL-3-METHOXYPYRAZINE 99+%
• butylmethoxypyrazine,2-sec-butyl-3-methoxypyrazine,2-methoxy-3-(sec-butyl)-pyrazine,3-S-BUTYL-2-METHOXYPYRAZINE,2-SEC-BUTYL-3-METHOXYPYRAZINE 99%
• 2-Ethoxypyrazine
• 3-Methyl-2-methoxypyrazine
• 2-ETHOXY-3-METHYLPYRAZINE
• 2-Isopropyl-3-methoxypyrazine
• 2-AMINO-5-METHOXYPYRAZINE
• 2-BROMO-5-METHOXYPYRAZINE
• 2,3-Dimethoxyquinoxaline
• 2-ETHOXY-3-ISOPROPYLPYRAZINE