2-Methoxypyrazine

2-Methoxypyrazine Basic information
Description References
Product Name:2-Methoxypyrazine
Synonyms:METHOXYPYRAZINE;METHOXYPYRAZINE, 2-;FEMA 3302;FEMA NUMBER 3302;methoxy-pyrazin;2-METHOXYPYRAZINE;2-METHOXYPYRAZINE 99+% FCC;2-Methoxypyrazine,98%
CAS:3149-28-8
MF:C5H6N2O
MW:110.11
EINECS:221-579-8
Product Categories:Building Blocks;Heterocyclic Building Blocks;Alkoxypyrazines;pyrazine Flavor;Alphabetical Listings;Flavors and Fragrances;Pyrazine;Pyrazines;M-N
Mol File:3149-28-8.mol
2-Methoxypyrazine Structure
2-Methoxypyrazine Chemical Properties
Boiling point 60-61 °C/29 mmHg (lit.)
density 1.14 g/mL at 25 °C (lit.)
FEMA 3302 | METHOXYPYRAZINE
refractive index n20/D 1.509(lit.)
Fp 114 °F
storage temp. Sealed in dry,Room Temperature
pka0.53±0.10(Predicted)
form clear liquid
color Colorless to Almost colorless
Specific Gravity1.140
Odorat 1.00 % in dipropylene glycol. sweet nutty cocoa
Odor Typechocolate
JECFA Number787
BRN 2241
LogP0.75
CAS DataBase Reference3149-28-8(CAS DataBase Reference)
NIST Chemistry ReferencePyrazine, methoxy-(3149-28-8)
EPA Substance Registry SystemPyrazine, 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 Information
ProviderLanguage
2-Methoxypyrazine English
SigmaAldrich English
ALFA English
2-Methoxypyrazine Usage And Synthesis
Description2-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.
ReferencesMurray, 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.



DescriptionMethoxypyrazine has an odor threshold of 700 ppb in water. Methoxypyrazine may be prepared from 2-hydroxypyrazine by various routes.
Chemical PropertiesMethoxypyrazine 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 PropertiesColorless liquid
OccurrencePresent 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.
DefinitionChEBI: Methoxypyrazine is an aromatic ether and a member of pyrazines.
PreparationFrom 2-hydroxypyrazine by various routes.
Aroma threshold values700 ppb in water
Safety ProfileSkin and eye irritant. When heated to decomposition it emits toxic fumes of NOx.
2-Methylpyrazine 2-METHYL-3-ISOPROPOXYPYRAZINE 2-ethoxy-5-methylpyrazine 2-METHYL-6-PROPOXYPYRAZINE 2-Isopropyl-5-methoxypyrazine,2-Isopropyl-6-methoxypyrazine,2-Isopropyl-3-methoxypyrazine 2,3-Dimethoxyquinoxaline Pyrazine, 2-methoxy-6-(1-methylpropyl)- 2-Methoxypyrazine 2-methoxy-6-methylpyrazine Tetramethylpyrazine 2-methoxy-5-methylpyrazine 2-Ethoxypyrazine butylmethoxypyrazine,2-sec-butyl-3-methoxypyrazine,2-methoxy-3-(sec-butyl)-pyrazine,3-S-BUTYL-2-METHOXYPYRAZINE,2-SEC-BUTYL-3-METHOXYPYRAZINE 99% Pyrazinamide 2-ETHOXY-3-ETHYLPYRAZINE Sulfachoropyrazine sodium 2-ETHOXY-3-ISOPROPYLPYRAZINE Glipizide

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