Wikipedia

Acetylpyrazine

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

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 Edit this at Wikidata
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)[2]
Boiling point 78–79 °C (172–174 °F; 351–352 K) (8 mmHg)[1]
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).

Natural occurrence

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

Uses

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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

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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

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  1. ^ a b Acetylpyrazine on Chemical Book
  2. ^ a b Acetylpyrazine on Sigma Aldrich
  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. ^ National Academies of Sciences, Engineering, and Medicine; Health And Medicine, Division; Board on Population Health and Public Health Practice; Committee on the Review of the Health Effects of Electronic Nicotine Delivery Systems; Eaton, D. L.; Kwan, L. Y.; Stratton, K. (2018). Stratton, Kathleen; Kwan, Leslie Y.; Eaton, David L. (eds.). Public Health Consequences of E-Cigarettes. doi:10.17226/24952. ISBN 978-0-309-46834-3. PMID 29894118. {{cite book}}: |website= ignored (help)CS1 maint: multiple names: authors list (link)
  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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