methyl ethoxypyrazine

Methyl ethoxypyrazine, systematically referred to as 2-methyl-3(or 5 or 6)-ethoxypyrazine, is a heterocyclic aromatic compound with the molecular formula C₇H₁₀N₂O. This pyrazine derivative is characterized by a distinctive nutty and earthy aroma, accompanied by flavor notes reminiscent of almond and toasted hazelnut. Synonyms include 2-ethoxymethylpyrazine and various mixtures of its isomers with methyl substitution at different positions on the pyrazine ring. It is naturally present or synthetically produced for use as a flavoring agent, contributing to the sensory profile of diverse food products. The compound's structural and chemical data are well documented in public chemical databases such as PubChem. Methyl ethoxypyrazine is typically derived through chemical synthesis methods tailored to preserve its volatility and sensory potency.

Methyl ethoxypyrazine is a pyrazine found in trace amounts within certain natural food sources and is most often employed synthetically in flavor formulations. It is recognized by FEMA (US) with the number 3569, indicating its acceptance for specified flavoring uses in the food industry. Its presence contributes nutty, almond, toasted almond, and earthy characteristics to complex flavor profiles, commonly in products such as beverages, confectionery, and dairy items. The compound's sensory notes of hazelnut and pineapple also support its application in specialty flavor blends. Regulatory evaluations ensure safe usage levels for food flavoring purposes under applicable standards.

Methyl ethoxypyrazine exhibits a molecular weight of approximately 138.17 g/mol and a chemical formula of C₇H₁₀N₂O. It is a clear liquid with a specific gravity range of 1.034 to 1.041 at 25 °C and a refractive index between 1.493 and 1.497 at 20 °C. The compound boils at roughly 175 to 176 °C under standard atmospheric pressure and has a moderate vapor pressure near 0.746 mmHg at 25 °C. Its flash point is recorded at 150 °F (~65.6 °C), indicating moderate volatility and flammability. Methyl ethoxypyrazine is soluble in alcohol and water, favoring formulation versatility. The estimated partition coefficient (log P) of 0.671 suggests moderate lipophilicity, influencing its behavior in various flavor matrices and extraction processes.

	2-(ethoxymethyl)pyrazine
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	103404
Pubchem (sid):	135270052

(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
FDA Substances Added to Food (formerly EAFUS):	View
HMDB (The Human Metabolome Database):	Search
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. 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:
flavoring agents
Recommendation for methyl ethoxypyrazine usage levels up to:
	not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU):		0.055 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA):		0.01 (μg/capita/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: 11
Click here to view publication 11
		average usual ppm	average maximum ppm
baked goods:		-	-
beverages(nonalcoholic):		-	0.50000
beverages(alcoholic):		-	-
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		-	-
condiments / relishes:		-	-
confectionery froastings:		-	2.00000
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		-	0.50000
fruit ices:		-	-
gelatins / puddings:		-	3.00000
granulated sugar:		-	-
gravies:		-	-
hard candy:		-	-
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):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) on a request from the Commission related to Flavouring Group Evaluation 17 (FGE.17): Pyrazine derivatives from chemical group 24 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf

Flavouring Group Evaluation 50 (FGE.50): Consideration of pyrazine derivatives evaluated by JECFA (57th meeting) structurally related to pyrazine derivatives evaluated by EFSA in FGE.17 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf

Flavouring Group Evaluation 17, Revision 1 (FGE.17Rev1): Pyrazine derivatives from chemical group 24 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) [1] View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 17, Revision 2 (FGE.17Rev2): Pyrazine derivatives from chemical group 24 View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 50, Revision 1 (FGE.50Rev1): Consideration of pyrazine derivatives evaluated by JECFA (57th meeting) structurally related to pyrazine derivatives evaluated by EFSA in FGE.17Rev2 (2010) View page or View pdf

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EPA Substance Registry Services (TSCA):65504-94-1

EPA ACToR:Toxicology Data

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Laboratory Chemical Safety Summary :103404

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:3

2-(ethoxymethyl)pyrazine

Chemidplus:0065504941