Acetylpyrazine
Names
Preferred IUPAC name
1-(Pyrazin-2-yl)ethan-1-one
Other names
2-Acetylpyrazine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.040.670
UNII
  • InChI=1S/C6H6N2O/c1-5(9)6-4-7-2-3-8-6/h2-4H,1H3
    Key: DBZAKQWXICEWNW-UHFFFAOYSA-N
  • InChI=1/C6H6N2O/c1-5(9)6-4-7-2-3-8-6/h2-4H,1H3
    Key: DBZAKQWXICEWNW-UHFFFAOYAU
  • CC(=O)C1=NC=CN=C1
Properties
C6H6N2O
Molar mass 122.127 g·mol−1
Appearance Yellow-brown powder
Melting point 75–78 °C (167–172 °F; 348–351 K)[1]
Boiling point 78–79 °C (172–174 °F; 351–352 K) (8 mmHg)[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Acetylpyrazine is an organic compound with the chemical formula C
6H
6N
2O. It is a yellow-brown powder at room temperature.[2] Chemically, acetylpyrazine is a pyrazine and a ketone.[1]

Natural occurrence

Acetylpyrazine is found in foods such as seeds, nuts and meats.

Uses

It is used in frozen dairy products such as ice cream.

It is considered generally recognized as safe by the U.S. Food and Drug Administration.[3]

"Essence formula for increasing cigarette fragrance and improving smoke quality".[4]

It is also known to be part of the formulation of e-cigarettes (vapes):[5]

Synthesis

Note that modern synthesis is for 2-cyanopyrazine from 2-methylpyrazine [109-08-0].[6][7]

Patent ("Popcorn-like flavor and aroma"):[8] Earlier patent:[9]

Pyrazinamide [98-96-4] (1) 2-Cyanopyrazine [19847-12-2] (2)

More modern syntheses have also been reported in recent years:[10][11][12]

References

  1. 1 2 Acetylpyrazine on Sigma Aldrich
  2. 1 2 Acetylpyrazine on Chemical Book
  3. ↑ Martin, Terry (8 Feb 2004). "Acetylpyrazine". About.com Smoking Cessation. Archived from the original on 6 January 2016. Retrieved 16 June 2014.
  4. ↑ Mao Deshou, et al. CN115216363 (2022 to China Tobacco Yunnan Industrial Co Ltd).
  5. ↑ Public Health Consequences of E-Cigarettes. NAP.edu.
  6. ↑ Rao, K. Narasimha; Gopinath, Rajesh; Prasad, P. S. Sai (2001). "Highly selective molybdenum phosphate catalyst for the ammoxidation of 2-methylpyrazine to 2-cyanopyrazine". Green Chemistry. 3 (1): 20–22. doi:10.1039/b005643j.
  7. ↑ Hong, Chun; Li, Yong (2006). "2-Cyanopyrazine Prepared from 2-Methylpyrazine by Catalytic Ammoxidation on MoVPO Catalyst". Chinese Journal of Chemical Engineering. 14 (5): 670–675. doi:10.1016/S1004-9541(06)60133-X.
  8. ↑ Donald L Roberts, U.S. Patent 3,402,051 (1968 to RJ Reynolds Tobacco Co).
  9. ↑ Jr Victor K Smith & Kushner Samuel, U.S. Patent 2,677,686 (1954 to Wyeth Holdings LLC).
  10. ↑ Mao, Lin; Niu, Dong-Fang; Hu, Shuo-Zhen; Zhang, Xin-Sheng (2022-05-28). "Electrochemical Synthesis of Acetylpyrazine". Journal of Electrochemistry. 28 (5): 2107061. doi:10.13208/j.electrochem.210706.
  11. ↑ Wang et al.: Progress in the Synthesis and Application of Acetylpyrazine, 2011.
  12. ↑ 任伟, et al. CN106588785 (2017 to Yoshida Spice Ltd By Share Ltd Shandong).
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