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Acetylpyrazine

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Acetylpyrazine Basic information
Product Name:Acetylpyrazine
Synonyms:ACETYLPYRAZINE;ACETYLPYRAZINE, 2-;2-ACETYLPYRAZINE;1-PYRAZIN-2-YLETHAN-1-ONE;1-PYRAZIN-2-YL-ETHANONE;METHYL PYRAZINYL KETONE;METHYL-2-PYRAZINYL KETONE;FEMA 3126
CAS:22047-25-2
MF:C6H6N2O
MW:122.12
EINECS:244-753-5
Product Categories:Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Chloropyrazines, etc.;pyrazine Flavor;Sulfides flavors;Building Blocks;Heterocyclic Building Blocks;Pyrazine;Heterocyclic Compounds;Miscellaneous;Pyrazines;Pharmaceutical Intermediates;ACETYLGROUP;22047-25-2
Mol File:22047-25-2.mol
Acetylpyrazine Structure
Acetylpyrazine Chemical Properties
Melting point 76-78 °C (lit.)
Boiling point 78-79°C 8mm
density 1.1075
FEMA 3126 | ACETYLPYRAZINE
refractive index 1.5350 (estimate)
Fp 78-79°C/8mm
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Methanol (Slightly)
pka0.30±0.10(Predicted)
form Solid
color White to Off-White
Odorpopcorn-like odor
Odor Typepopcorn
biological sourcesynthetic
JECFA Number784
BRN 109630
Major Applicationflavors and fragrances
Cosmetics Ingredients FunctionsPERFUMING
InChI1S/C6H6N2O/c1-5(9)6-4-7-2-3-8-6/h2-4H,1H3
InChIKeyDBZAKQWXICEWNW-UHFFFAOYSA-N
SMILESCC(=O)c1cnccn1
LogP0.20
CAS DataBase Reference22047-25-2(CAS DataBase Reference)
NIST Chemistry ReferenceAcetylpyrazine(22047-25-2)
EPA Substance Registry SystemEthanone, 1-pyrazinyl- (22047-25-2)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-24/25
WGK Germany 2
TSCA TSCA listed
HazardClass IRRITANT
HS Code 29339900
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
2-Acetylpyrazine English
ACROS English
ALFA English
Acetylpyrazine Usage And Synthesis
Description2-acetylpyrazine is white to pale yellow crystalline powder with a nutty, popcorn, bread-crust odor. It is soluble in water and stable under ordinary conditions. It is used to manufacture many polycyclic compounds and used as useful structures in pharmaceuticals and perfumes. It is a component of the folates (vitamin B compounds) and of the isoalloxazine ring nucleus of flavins. Numerous pyrazine derivatives such as pyrazine polycyclic compounds, alkyl-, alicyclic-, and alkylaryl-substituted compounds, derivatives containing oxygenated functional groups and thio-functional groups in the side-chains are used in biological, drug, flavoring and perfumery industry. 2-acetylpyrazine is used as food additive, commonly used in chocolate and baked goods.
Chemical PropertiesAcetylpyrazine is a light yellow to yellow-brownish powder that has a nutty, popcorn, bread crust odor. It is one of the volatile aroma components in popcorn, wheat and rye crusts.
OccurrenceReported found in guava fruit (Psidium guajava L.), wheaten bread, other types of breads, boiled and cooked beef, grilled/roasted uncured pork, pork liver, cocoa, coffee, black tea, roasted barley, roasted filbert (Corylus avellano), roasted peanut (Arachis hypogea), roasted almond (Prunus amygdalus), scallop, filberts, popcorn and sesame oil.
UsesAcetylpyrazine has been used in synthesis of:
7-heteroaryl-pyrazolo[1,5-a]pyrimidine-3-carboxamides
copper (II) complexes with di-imine ligands
N(4) substituted thiosemicarbazones
DefinitionChEBI: 2-acetylpyrazine is a pyrazine that is substituted by an acetyl group at position 2. It has been identified as one of the volatile flavor constituents in popcorn, bread crust, vinegar, and potato snacks. It has a role as a flavouring agent. It is an aromatic ketone and a member of pyrazines.
ApplicationAcetylpyrazine has been widely used as an intermediate in the organic synthesis of various heterocyclic derivatives and in coupling reactions, alkylation reactions, and sensitizer ligands because of its good biological and reactive activities. For example, it is a significant reaction intermediate for producing drugs for treating malaria, epilepsy, and Parkinson's disease.
Preparationsynthesis of acetylpyrazine: By the ester condensation of EtO2 C-pyrazine; by dehydrating pyrazynamide with POCI3 and then reacting the resulting 2-cyano-pyrazine with methyl magnesium bromide.
Aroma threshold valuesDetection at 62 ppb
Taste threshold valuesTaste characteristics at 10 ppm: roasted, nutty, bready, yeasty with popcorn, corn chip nuance
General Description2-Acetylpyrazine has been identified as one of the volatile flavor constituents in popcorn, wheat and rye bread crust.
Synthesis
Ethylpyrazine

13925-00-3

Acetylpyrazine

22047-25-2

General procedure: 2-ethylpyrazine (0.5 mmol), MnOx-N(at)C catalyst (1 mg, pyrolyzed at 600 °C) and tert-butyl hydroperoxide (TBHP, 1.5 mmol, 65% aqueous solution) were added to a 15 mL round bottom flask (RBF). After sealing the flask, the reaction mixture was heated and stirred at 60 °C for 12 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was diluted with ethyl acetate (4 mL), followed by centrifugation at 10,000 r/min for 1 min to separate the catalyst. The supernatant was collected and the catalyst was washed with ethyl acetate (5 x 4 mL). The supernatant and washings were combined and concentrated to dryness under reduced pressure, and the resulting residue was purified by rapid column chromatography on silica gel (eluent: ethyl acetate/hexane = 1:10, v/v).

References[1] CHAO-RUI LI. Study on 2-Acetylpyrazine (pyridine-2-acetyl) hydrazone as a fluorescent sensor for Al3+[J]. Journal of Luminescence, 2015, 168: Pages 330-333. DOI:10.1016/j.jlumin.2015.07.055.
[2] RAMAIYER VENKATRAMAN. Structures of Eight Thio(semi)carbazones Derived from 2-Acetylpyrazine, 2-Acetythiazole and Acetophenone[J]. Journal of Chemical Crystallography, 2009, 39 10. DOI:10.1007/s10870-009-9541-0.
[3] LIN MAO. Electrochemical Synthesis of Acetylpyrazine[J]. Journal of Electrochemistry, 2021, 9 1: 0. DOI:10.13208/J.ELECTROCHEM.210706.
[4] https://pubchem.ncbi.nlm.nih.gov/compound/Acetylpyrazine#section=Pharmacology-and-Biochemistry
[5] https://en.wikipedia.org/wiki/Acetylpyrazine
[6] http://www.chemicalland21.com/specialtychem/perchem/2-ACETYLPYRAZINE.htm
Tag:Acetylpyrazine(22047-25-2) Related Product Information
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