| Identification | More | [Name]
Acetylpyrazine | [CAS]
22047-25-2 | [Synonyms]
1-PYRAZIN-2-YLETHAN-1-ONE
1-PYRAZIN-2-YL-ETHANONE
2-ACETYLPYRAZINE
ACETYLPYRAZINE
ACETYLPYRAZINE, 2-
FEMA 3126
FEMA NUMBER 3126
METHYL-2-PYRAZINYL KETONE
METHYL PYRAZINYL KETONE
TIMTEC-BB SBB006738
1-(2-Pyrazinyl)ethanone
1-pyrazinyl-ethanon
1-pyrazinylethanone
1-pyrazinyl-Ethanone
Ethanone, 1-pyrazinyl-
Ethanone,1-pyrazinyl-
Ketone, methyl pyrazinyl
Ketone,methylpyrazinyl
pyrazin-1-ylethan-1-one
Metyl 2-pyrazinyl ketone | [EINECS(EC#)]
244-753-5 | [Molecular Formula]
C6H6N2O | [MDL Number]
MFCD00006134 | [Molecular Weight]
122.12 | [MOL File]
22047-25-2.mol |
| Chemical Properties | Back Directory | [Appearance]
LIGHT YELLOW TO YELLOW-BROWNISH POWDER | [Melting point ]
76-78 °C (lit.) | [Boiling point ]
78-79°C 8mm | [density ]
1.1075 | [FEMA ]
3126 | [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) | [form ]
Solid | [pka]
0.30±0.10(Predicted) | [color ]
White to Off-White | [Odor]
popcorn-like odor | [biological source]
synthetic | [Odor Type]
popcorn | [JECFA Number]
784 | [BRN ]
109630 | [Major Application]
flavors and fragrances | [Cosmetics Ingredients Functions]
PERFUMING | [InChI]
1S/C6H6N2O/c1-5(9)6-4-7-2-3-8-6/h2-4H,1H3 | [InChIKey]
DBZAKQWXICEWNW-UHFFFAOYSA-N | [SMILES]
CC(=O)c1cnccn1 | [LogP]
0.20 | [CAS DataBase Reference]
22047-25-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Acetylpyrazine(22047-25-2) | [EPA Substance Registry System]
22047-25-2(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
2
| [Hazard Note ]
Irritant | [TSCA ]
T | [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
2-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 Properties]
Acetylpyrazine has a nutty, popcorn, bread crust odor. | [Chemical Properties]
LIGHT YELLOW TO YELLOW-BROWNISH POWDER | [Occurrence]
Reported 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. | [Uses]
Acetylpyrazine 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
| [Application]
Acetylpyrazine 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. | [Definition]
ChEBI: 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. | [Preparation]
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 values]
Detection at 62 ppb | [Taste threshold values]
Taste characteristics at 10 ppm: roasted, nutty, bready, yeasty with popcorn, corn chip nuance | [General Description]
2-Acetylpyrazine has been identified as one of the volatile flavor constituents in popcorn, wheat and rye bread crust. | [Synthesis]
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). | [storage]
Store at -20°C | [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 |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
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