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2-acetyl pyrazine

Chemical Structure

General Material Information

Preferred name 2-acetyl pyrazine
Trivial Name Acetylpyrazine
Short Description 1-pyrazin-2-ylethanone
Formula C6 H6 N2 O
CAS Number 22047-25-2
Deleted CAS Number 131922-02-6
FEMA Number 3126
Flavis Number 14.032
ECHA Number 244-753-5
FDA UNII GR391IBU5C
Nikkaji Number J27.905F
MDL MFCD00006134
COE Number 2286
NMR Predictor External link
JECFA Food Flavoring 784 2-acetylpyrazine
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 22047-25-2 ; ACETYLPYRAZINE
Synonyms
  • acetyl pyrazine
  • 2-acetyl pyrazine
  • 2-acetyl pyrazine FCC
  • acetyl-2 pyrazine
  • 2-acetylpyrazine
  • 2 acetylpyrazine
  • 2-acetylpyrazine FCC
  • ethanone, 1-(2-pyrazinyl)-
  • ethanone, 1-pyrazinyl-
  • ketone, methyl pyrazinyl
  • methyl 2-pyrazinyl ketone
  • methyl pyrazin-2-yl ketone
  • methyl pyrazinyl ketone
  • methyl-2-pyrazinyl ketone
  • methylpyrazinyl ketone
  • popcorn pyrazine
  • pyrazin-1-ylethan-1-one
  • 1-pyrazin-2-yl-ethanone
  • 1-( pyrazin-2-yl)ethan-1-one
  • 1-( pyrazin-2-yl)ethanone
  • 1-pyrazin-2-ylethan-1-one
  • 1-pyrazin-2-ylethanone
  • pyrazine, 2-acetyl
  • pyrazine, 2-acetyl-
  • 1-pyrazinylethanone
  • 1-pyrazin-2-ylethanone
  • 1-(2-Pyrazinyl)ethanone
  • 2-Acetylpyrazine
  • Acetylpyrazine
  • Pyrazine methyl ketone
  • NSC 72374
  • 1-(Pyrazin-2-yl)ethanone
  • 1-(2-Pyrazinyl)-1-ethanone
  • 2-Acetyl-1,4-pyrazine

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

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Literature & References

1-pyrazin-2-ylethanone
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:22047-25-2
Pubchem (cid):30914
Pubchem (sid):134993897
Flavornet:22047-25-2
Publications by Perfumer & Flavorist
Flavor Bites: 2-Acetyl Pyrazine
Publications by US Patents
3,952,024 - Furfurylthioacetone
3,931,166 - Certain 2,5-dimethyl-3-thiopyrazines
Publications by PubMed
Identification of potent odorants formed during the preparation of extruded potato snacks.
Gas chromatography-olfactometry and chemical quantitative study of the aroma of six premium quality spanish aged red wines.
How low pH can intensify beta-damascenone and dimethyl trisulfide production through beer aging.
Main group bismuth(III), gallium(III) and diorganotin(IV) complexes derived from bis(2-acetylpyrazine)thiocarbonohydrazone: synthesis, crystal structures and biological evaluation.
Synthesis, crystal structures, in vitro biological evaluation of zinc(II) and bismuth(III) complexes of 2-acetylpyrazine N(4)-phenylthiosemicarbazone.
Cytotoxicity and structure-activity relationships of four alpha-N-heterocyclic thiosemicarbazone derivatives crystal structure of 2-acetylpyrazine thiosemicarbazone.
(E)-2-Acetyl-pyrazine 4-nitro-phenyl-hydrazone.
Effect of cysteine and cystine addition on sensory profile and potent odorants of extruded potato snacks.
2-Acetyl-pyrazine 4-methyl-thio-semi-carbazone.
New Ag(I)-containing coordination polymers generated from multidentate Schiff-base ligands.
Solvent-free reactions of C60 with active methylene compounds, either with or without carbon tetrabromide, in the presence of bases under high-speed vibration milling conditions.
2-benzoxazolyl and 2-benzimidazolyl hydrazones derived from 2-acetylpyridine: a novel class of antitumor agents.
Studies on pyrazine derivatives--XXXIV. Synthesis and tuberculostatic activity of alpha-oxo ketene dithioacetals pyrazine derivatives.
Measurement of interactions between polysaccharides and flavour compounds by exclusion size chromatography: advantages and limits.

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):HMDB31861
FooDB:FDB008545
Export Tariff Code:2933.99.9700
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

Suppliers

Advanced Biotech Alfrebro
Ambles Nature et Chimie Anhui Haibei
Anhui Suzhou Jinli Aromatic Chemicals Apple Flavor & Fragrance
Augustus Oils Beijing Lys Chemicals
Berjé BOC Sciences
Charkit Chemical Citrus and Allied Essences
De Monchy Aromatics DeLong Chemicals America
Diffusions Aromatiques Elan Inc.
Endeavour Specialty Chemicals Ernesto Ventós
FCI SAS Fleurchem
Frutarom H. Interdonati, Inc.
IFF Indukern F&F
Jiangyin Healthway Jinan Enlighten Chemical Technology(Wutong Aroma )
Kingchem Laboratories Lluch Essence
M&U International Moellhausen
Oamic Ingredients Omega Ingredients
Pearlchem Corporation Penta International
Phoenix Aromas & Essential Oils Prodasynth
R C Treatt & Co Ltd Reincke & Fichtner
Riverside Aromatics Robinson Brothers
Santa Cruz Biotechnology Sigma-Aldrich
SRS Aromatics Sunaux International
Synerzine Taytonn ASCC
TCI AMERICA Tengzhou Jitian Aroma Chemiclal
Tengzhou Xiang Yuan Aroma Chemicals The Lermond Company
Tianjin Danjun International United International
Vigon International WEN International
WholeChem Advanced Biotech. Inc.
Alfrebro LLC/ Archer Daniels Midland Company Augustus Oils Ltd
Beijing Lys Chemicals Co, LTD. Berje Inc.
Charkit Chemical Corporation Endeavour Specialty Chemicals Ltd
Fleurchem, Inc. FRUTAROM USA INC,
Indukern, S.A. F&F Ingredients Division Jiangyin Healthway International Trade Co., Ltd
Lluch Essence S.L. M&U International LLC
Moellhausen S.P.A. Penta International Corporation
Riverside Aromatics Ltd. Robinson Brothers Limited
SRS Aromatics Ltd Synerzine, Inc.
Taytonn ASCC Pte Ltd Tianjin Danjun International Trade Co., LTD.
R C Treatt and Co Ltd Qingdao Free Trade Zone United International Co Ltd
Ernesto Ventós S.A. WholeChem, LLC

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 122.12702178955
Melting Point 76 to 78°C @ 760 mm Hg
Boiling Point 188 to 190°C @ 760 mm Hg
Vapor Pressure 0.188 mmHg @ 25 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 0.2
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
dipropylene glycol Yes
water, 6.652e+004 mg/L @ 25 °C (est) Yes
water, 6.65E+04 mg/L @ C (exp) Yes

Organoleptic Properties

Odor Type: Popcorn
popcorn, nutty, corn chip, bread crust, chocolate, hazelnut, coffee, musty, roasted, potato
Odor strength very high , recommend smelling in a 0.10 % solution or less
Substantivity 400 hour(s) at 10.00 % in dipropylene glycol
Luebke, William tgsc, (1996) At 0.10 % in propylene glycol. popcorn nutty corn chip bread crust chocolate hazelnut coffee
Mosciano, Gerard P&F 17, No. 1, 41, (1992) Musty, roasted, corn chip, popcorn, nutty and potato-like
Flavor Type: Roasted
roasted, nutty, bready, yeasty, popcorn, corn chip
Mosciano, Gerard P&F 17, No. 1, 41, (1992) At 10.00 ppm. Roasted, nutty, bready and yeasty, with popcorn and corn chip nuances
Used not only for popcorn type flavours, but also in roast nut flavours (hazelnut, peanut, almond), chocolate, bread and yeast type flavors. 2-Acetylpyrazine and 2-acetylthiazole both have aromas similar to the non-GRAS material 2-acetylpyrroline which is an important character impact compound in aromatic rice, bread crust and popcorn. Normal use levels in finished consumer product: 0.05-5 ppm. Council of Europe limits: foods (5 ppm); beverages (5 ppm). Nutty
General comment Chocolate, popcorn in dilution (10ppm)

Occurrences

Safety Information

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 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Skin irritation (Category 2), H315
Eye irritation (Category 2A), H319
Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335
GHS Label elements, including precautionary statements
Pictogram
Signal word Warning
Hazard statement(s)
H315 - Causes skin irritation
H319 - Causes serious eye irritation
H335 - May cause respiratory irritation
Precautionary statement(s)
P261 - Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 - Wash skin thouroughly after handling.
P271 - Use only outdoors or in a well-ventilated area.
P280 - Wear protective gloves/protective clothing/eye protection/face protection.
P302 + P352 - IF ON SKIN: wash with plenty of soap and water.
P304 + P340 - IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P312 - Call a POISON CENTER or doctor/physician if you feel unwell.
P332 + P313 - IF SKIN irritation occurs: Get medical advice/attention.
P337 + P313 - IF eye irritation persists: Get medical advice/attention.
P362 - Take off contaminated clothing and wash before reuse.
P403 + P233 - Store in a well-ventilated place. Keep container tightly closed.
P405 - Store locked up.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Oral/Parenteral Toxicity:
gavage-rat LD50 [sex: M,F] > 3000 mg/kg
(Posternak et al., 1975)

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-acetyl pyrazine usage levels up to:
0.0500 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 12.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 120.00 (μg/capita/day)
Structure Class: II
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: -5.00000
beverages(nonalcoholic): -5.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -5.00000
fruit ices: -5.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -5.00000
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):

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

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):22047-25-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :30914
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
1-pyrazin-2-ylethanone
Chemidplus:0022047252