2-methoxy-3-methyl pyrazine

2-methoxy-3-methyl pyrazine is a heterocyclic organic compound belonging to the class of pyrazine derivatives. This compound appears as a colorless to pale yellow liquid with a molecular formula of C₆H₈N₂O and a molecular weight of approximately 124.14 g/mol. Known under various synonyms such as almond pyrazine and 2-methoxy-3-methyl-pyrazine, it is notable for its characteristic roasted almond, hazelnut, and peanut-like aroma at low concentrations. The compound is extensively utilized in flavor and fragrance formulations to impart nutty, chocolate, and green notes. It is typically sourced through chemical synthesis methods designed to reproduce the naturally occurring pyrazines found in smoked wood and certain food products. More structured data about this compound can be found in public chemical databases like PubChem which provides detailed molecular information and safety data.

2-methoxy-3-methyl pyrazine naturally occurs in wood smoke and contributes to its characteristic aroma. It plays a significant role as a flavor and fragrance agent and is applied widely within the food and cosmetic industries. Key applications include use in coffee, hazelnut, and peanut flavor formulations as well as enhancement of almond and toasted almond notes in various products. Furthermore, it finds use in perfuming agents, demonstrating versatility across multiple product forms. The compound’s usage follows IFRA (Global) regulations, which recommend a maximum concentration of 0.1% in fragrance concentrates to ensure safety in consumer products. Additionally, 2-methoxy-3-methyl pyrazine is recognized by FEMA (US) with the number 3183, underscoring its acceptance as a flavoring substance.

2-methoxy-3-methyl pyrazine exhibits several physicochemical characteristics that influence its behavior in formulations. It has a boiling point ranging from 158 to 159°C at standard atmospheric pressure, and a moderate vapor pressure of 3.271 mmHg at 25°C, which affects its volatility and release profile in flavor and fragrance blends. The compound’s specific gravity ranges between 1.081 and 1.085 at 25°C, and its refractive index spans from 1.504 to 1.508 at 20°C, indicating liquid density and optical properties relevant to quality control. It displays a logP value of approximately 1.24, suggesting moderate lipophilicity that facilitates solubility in alcohols, though it shows limited solubility in water. Despite being soluble in alcohol and estimated water solubility at about 8457 mg/L at 25°C, it is generally considered to have low aqueous solubility, which impacts its incorporation into aqueous products. The flash point is approximately 132°F (about 56°C), a critical safety parameter during handling and processing.

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
CHEMBL:	View
HMDB (The Human Metabolome Database):	Search
FooDB:	FDB008536
Export Tariff Code:	2933.90.8000
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed. R 37/38 - Irritating to respiratory system and skin. R 41 - Risk of serious damage to eyes. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 37/39 - Wear suitable gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 2-methoxy-3-methyl pyrazine usage levels up to:
	0.1000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU):		12.00 (μg/capita/day)
Threshold of Concern:		90 (μg/person/day)
Structure Class:		III
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 4
Click here to view publication 4
		average usual ppm	average maximum ppm
baked goods:		-	4.00000
beverages(nonalcoholic):		-	-
beverages(alcoholic):		-	-
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		-	-
condiments / relishes:		-	-
confectionery froastings:		-	-
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		-	2.00000
fruit ices:		-	2.00000
gelatins / puddings:		-	2.00000
granulated sugar:		-	-
gravies:		-	-
hard candy:		-	4.00000
imitation dairy:		-	-
instant coffee / tea:		-	-
jams / jellies:		-	-
meat products:		-	-
milk products:		-	-
nut products:		-	-
other grains:		-	-
poultry:		-	-
processed fruits:		-	-
processed vegetables:		-	-
reconstituted vegetables:		-	-
seasonings / flavors:		-	-
snack foods:		-	-
soft candy:		-	-
soups:		-	-
sugar substitutes:		-	-
sweet sauces:		-	-

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Scientific Opinion on Flavouring Group Evaluation 17, Revision 3 (FGE.17Rev3): Pyrazine derivatives from chemical group 24 View page or View pdf

Safety and efficacy of pyrazine derivatives including saturated ones belonging to chemical group 24 when used as flavourings for all animal species View page or View pdf

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):2847-30-5

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :17898

National Institute of Allergy and Infectious Diseases:Data

WISER:UN 1993

WGK Germany:3

2-methoxy-3-methylpyrazine

Chemidplus:0002847305