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2-isobutyl-3,5-(and 3,6)-dimethyl pyrazine

2-isobutyl-3,5-(and 3,6)-dimethyl pyrazine is a pyrazine derivative with cocoa and nutty aroma notes used as a flavor and fragrance agent in various industries.

General Material Description

2-isobutyl-3,5-(and 3,6)-dimethyl pyrazine is an organic compound classified as a substituted pyrazine. It has the molecular formula C10H16N2 and is recognized for its characteristic cocoa and nutty odor profile. The material typically appears as a colorless to pale liquid with a distinct aroma reminiscent of roasted nuts and cocoa. Synonyms include 3,5- and 3,6-dimethyl-2-isobutylpyrazine and 3,5,6-trimethyl-2-isobutylpyrazine, reflecting positional isomers around the pyrazine ring. This compound is linked in chemical databases such as PubChem under various registry numbers. It is naturally found in foods like cocoa and potatoes and can be isolated or synthesized for use in flavor and fragrance applications.

Occurrence, Applicability & Potential Uses

This compound naturally occurs in various foods, notably cocoa and potatoes, contributing to their characteristic aroma profiles. Due to its potent odor properties, it is widely utilized as a flavor and fragrance agent imparting balsam, fern, floral, mossy, and oriental facets. It enhances chocolate or cocoa and nut flavors where a roasted, earthy note is desired. The International Fragrance Association (IFRA) provides guidelines for its usage in fragrance products to ensure safe application levels. Its inclusion in formulations extends to perfumes, flavorings in baked goods, dairy products, and processed vegetables, where it enriches sensory qualities.

Physico-Chemical Properties Summary

At 25 °C, 2-isobutyl-3,5-(and 3,6)-dimethyl pyrazine exhibits a specific gravity range of approximately 0.924 to 0.934, indicating a density slightly less than water. Its refractive index at 20 °C ranges from 1.489 to 1.494, consistent with aromatic heterocyclic compounds. The substance has a relatively low boiling point between 73 and 75 °C measured under reduced pressure (2 mm Hg), indicating volatility suitable for fragrance and flavor releases. It is soluble in alcohol but insoluble in water, influencing its solubility profile in various product formulations. These properties allow for effective integration into liquid and solid matrices where aroma delivery is essential.

FAQ

What is 2-isobutyl-3,5-(and 3,6)-dimethyl pyrazine?
2-isobutyl-3,5-(and 3,6)-dimethyl pyrazine is a heterocyclic aromatic compound classified as a substituted pyrazine. It is known for its distinctive cocoa, nutty, and roasted odor characteristics. This compound is used extensively in flavor and fragrance industries to impart these sensory qualities. It naturally appears in some foods such as cocoa and potatoes, contributing to their aroma profiles.
Where does 2-isobutyl-3,5-(and 3,6)-dimethyl pyrazine occur and how is it used?
This compound occurs naturally in cocoa beans and potatoes and forms part of their characteristic flavor and aroma. It is employed as a flavor and fragrance agent in multiple applications. Its odor profile includes balsam, fern, floral, moss, and oriental notes, making it valuable for enhancing chocolate and nut flavors in baked goods, dairy products, and processed vegetables. The compound’s solubility in alcohol but not water affects formulation strategies for effective use.
What are the regulatory and safety considerations for 2-isobutyl-3,5-(and 3,6)-dimethyl pyrazine?
According to IFRA (Global) guidelines, 2-isobutyl-3,5-(and 3,6)-dimethyl pyrazine is approved for use in fragrance concentrates up to 0.3%. It is recognized by FEMA (US) as a generally recognized as safe (GRAS) flavoring substance with established usage levels in various food categories, including baked goods and dairy. No significant hazards or precautionary statements are found under OSHA HCS classification. Safety data from EPA and related regulatory bodies do not indicate notable toxicity, but typical good handling practices in flavor and fragrance manufacturing apply.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Other Information

HMDB (The Human Metabolome Database):Search
FooDB:FDB009317
VCF-Online:VCF Volatile Compounds in Food

General Material Information

Trivial Name 2-isobutyl-3,5-(and 3,6)-dimethyl pyrazine
Short Description 3,5- and 3,6-dimethyl-2-isobutylpyrazine
Formula C10 H16 N2
CAS Number 38888-81-2
FEMA Number 4100
FDA UNII Search
JECFA Food Flavoring 2130 3,5- and 3,6-dimethyl-2-isobutylpyrazine
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 3,5- AND 3,6-DIMETHYL-2-ISOBUTYLPYRAZINE
Synonyms
  • 2-iso butyl-3,(5 and 6)-dimethylpyrazine
  • 2-iso butyl-3,5-(and 3,6)-dimethylpyrazine
  • 3,5-and 3,6-dimethyl-2-isobutyl pyrazine
  • 3,5-and 3,6-dimethyl-2-isobutylpyrazine
  • 3,5,6-dimethyl-2-isobutylpyrazine
  • 3,5-and 3,6-dimethyl-3-(2-methyl propyl) pyrazine
  • 3,5-and 3,6-dimethyl-3-(2-methyl propyl)-1,4-diazine

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 164.25152587891
Specific gravity @ 25 °C
Pounds per Gallon 7.689 to 7.772
Refractive Index 1.489 to 1.494 @ 20 °C
Boiling Point 73 to 75°C @ 2 mm Hg
Solubility
alcohol Yes
water No

Organoleptic Properties

Odor Type: Cocoa
cocoa, hazelnut, musty, earthy, roasted, nutty
General comment At 0.10 % in dipropylene glycol. cocoa hazelnut musty earthy roasted nutty

Occurrences

Potential Uses

Applications
Odor purposes Balsam , Fern , Floral , Moss , Oriental
Flavoring purposes Chocolate cocoa , Nut

Safety Information

Safety information

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-isobutyl-3,5-(and 3,6)-dimethyl pyrazine usage levels up to:
0.3000 % in the fragrance concentrate.
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: 22
Click here to view publication 22
average usual ppmaverage maximum ppm
baked goods: 1.500002.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: 1.500002.00000
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: 2.000003.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: 0.500001.50000
reconstituted vegetables: --
seasonings / flavors: 5.0000010.00000
snack foods: --
soft candy: --
soups: 0.500001.50000
sugar substitutes: --
sweet sauces: 2.000003.00000

Safety references

EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
National Institute of Allergy and Infectious Diseases:Data
Chemidplus:0038888812