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chocolate pyrazine B

Chocolate pyrazine B is 2-methoxy-3-methylpyrazine, a flavor compound with a nutty, roasted aroma used in food flavoring.
Chemical Structure

General Material Description

Chocolate pyrazine B, chemically known as 2-methoxy-3-methylpyrazine, is a heterocyclic aromatic organic compound with the molecular formula C6H8N2O. This compound is recognized for its distinctive nutty and roasted aroma reminiscent of hazelnut and barley. It appears as a volatile flavoring agent employed primarily for sensory enhancement in food products. Known by multiple synonyms including 2-methoxy-(3,6)-methylpyrazine and 3-methoxy-2-methylpyrazine, chocolate pyrazine B is indexed in controlled-vocabulary databases such as PubChem (CID 17898). It is typically derived synthetically or isolated from natural sources for use in flavor formulations. The compound’s characteristic sensory notes make it valuable in mimicking or complementing chocolate, coffee, and nut flavors.

Occurrence, Applicability & Potential Uses

This compound naturally occurs in various biological sources such as burdock root, fenugreek seed, krill, and sherry, indicating its relevance in both plant and marine-derived aromas. Chocolate pyrazine B is applied primarily as a flavoring agent, contributing nutty and roasted notes to foodstuffs. It enhances flavors including almond, caramel, chocolate, cocoa, coffee, hazelnut, nut, and peanut profiles. Its inclusion respects food safety standards such as FEMA GRAS (US), under which usage levels are regulated for specific foods like baked goods, frozen dairy, and confectionery frostings. Additionally, it serves in cosmetic applications as a perfuming agent, relying on its aromatic characteristics for fragrance formulation.

Physico-Chemical Properties Summary

Chocolate pyrazine B exhibits a moderate molecular weight of 124.14 g/mol and a molecular formula C6H8N2O. The compound’s physicochemical traits include a vapor density approximately 4.2 times that of air and a flash point near 54 °C (130 °F), reflecting moderate flammability. Its logP value of 1.24 signals balanced lipophilicity conducive to flavor use in a variety of matrices. Measured specific gravity ranges between 1.06 and 1.09 at 25 °C, with a refractive index from 1.505 to 1.51 at 20 °C. Vapor pressure is relatively low at 0.584 mmHg at 25 °C, indicative of moderate volatility suitable for aroma release. The compound is soluble in alcohol and moderately soluble in water (approximately 8457 mg/L at 25 °C), facilitating its incorporation into diverse formulations. These properties influence its distribution, stability, and sensory performance during product manufacturing and storage.

FAQ

What is chocolate pyrazine B and what are its main characteristics?
Chocolate pyrazine B is 2-methoxy-3-methylpyrazine, a flavor compound known for its nutty, roasted aroma reminiscent of hazelnut and barley. It belongs to the pyrazine chemical family, which consists of nitrogen-containing aromatic heterocycles. This compound is used primarily as a flavoring agent in food applications due to its distinctive sensory profile. It is identified by synonyms such as 2-methoxy-(3,6)-methylpyrazine and 3-methoxy-2-methylpyrazine, and has the molecular formula C6H8N2O. Chocolate pyrazine B is also referenced in databases like PubChem and FEMA (US).
Where does chocolate pyrazine B naturally occur and how is it used in products?
This compound naturally appears in burdock root, fenugreek seed, krill, and sherry, contributing to their characteristic flavors and aromas. It is employed as a flavoring additive to impart nutty and roasted notes to food products such as baked goods, confectionery frostings, frozen dairy, and fruit ices. Usage levels follow regulatory standards like FEMA GRAS (US) ensuring safe consumption. Besides food flavoring, chocolate pyrazine B is also used in perfuming agents within the cosmetic industry for its aromatic qualities.
What regulations and safety considerations apply to chocolate pyrazine B in flavor applications?
Chocolate pyrazine B complies with standards like FEMA GRAS (US) and is listed under ECHA reach pre-registration (EU). It has been evaluated by authoritative bodies including EFSA for use as a flavoring substance. Safety information highlights classification as harmful (Xn) with flammability concerns and irritation potential to eyes, respiratory system, and skin. Recommended exposure limits and usage concentrations vary by product type, with maximum levels established in baked goods and other applications. Proper handling includes wearing protective clothing and avoiding ingestion or contact with eyes.

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

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Other Information

(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
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB31852
FooDB:FDB008536
Export Tariff Code:2933.90
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

General Material Information

Preferred name chocolate pyrazine B
Trivial Name 2-Methoxy-3-methylpyrazine
Short Description 2-methoxy-(3,6)-methylpyrazine
Formula C6 H8 N2 O
CAS Number 2847-30-5
FEMA Number 3183
ECHA Number 220-651-6
FDA UNII 04O7CN9Q85
Nikkaji Number J100.520K
MDL MFCD00006127
COE Number 2266
NMR Predictor External link
JECFA Food Flavoring 788 2-methoxy-(3,5 or 6)-methylpyrazine
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 977044-49-7 ; (2 OR 5 OR 6)-METHOXY-3-METHYLPYRAZINE (MIXTURE OF ISOMERS)
Synonyms
  • 2-methoxy-(3,6)-methyl pyrazine
  • 2-methoxy-(3,6)-methylpyrazine
  • 2-methoxy-3-methyl pyrazine
  • 2-methoxy-3-methyl pyrazine + 2-methoxy-6-methyl pyrazine
  • 2-methoxy-3-methyl pyrazine + 5-methoxy-3-methyl pyrazine
  • 2-methoxy-3-methylpyrazine
  • 2-methoxy-3-methylpyrazine + 2-methoxy-6-methylpyrazine
  • 2-methoxy-3-methylpyrazine + 5-methoxy-3-methylpyrazine
  • 2-methoxy-3(5/6)-methyl pyrazine
  • 2-methoxy-3(5or 6)-methylpyrazine
  • 2-methoxy-3(6)-methyl pyrazine
  • Pyrazine, 2-methoxy-3-methyl-
  • 2-Methoxy-3-methylpyrazine
  • 2-Methyl-3-methoxypyrazine
  • 3-Methoxy-2-methylpyrazine

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 124.14295959473
Specific gravity @ 25 °C
Pounds per Gallon 8.82 to 9.07
Refractive Index 1.505 to 1.51 @ 20 °C
Vapor Pressure 0.584 mmHg @ 25 °C
Vapor Density 4.2
Flash Point TCC Value 54.44 °C TCC
logP (o/w) 1.24
Solubility
alcohol Yes
water, 8457 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Nutty
nutty, hazelnut roasted hazelnut, barley roasted barley, almond
General comment At 0.10 % in dipropylene glycol. nutty roasted hazelnut barly

Occurrences

Potential Uses

Applications
Flavoring purposes Almond , Almond toasted almond , Caramel , Chocolate cacao , Chocolate cocoa , Coffee , Hazelnut , Nut , Peanut
Cosmetic purposes Perfuming agents

Safety Information

Safety information

European information :
Most important hazard(s):
Xn - Harmful.
R 10 - Flammable.
R 22 - Harmful if swallowed.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, 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 chocolate pyrazine B usage levels up to:
not for fragrance use.
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 ppmaverage 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 Authority (EFSA) reference(s):

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