Acetylpropionyl

Acetylpropionyl, also known as acetyl propionyl or 2,3-pentanedione,[1] is an organic compound, specifically a diketone.[2]

Acetylpropionyl
Names
Preferred IUPAC name
Pentane-2,3-dione
Other names
2,3-Pentanedione
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.078
UNII
  • InChI=1S/C5H8O2/c1-3-5(7)4(2)6/h3H2,1-2H3
    Key: TZMFJUDUGYTVRY-UHFFFAOYSA-N
  • InChI=1/C5H8O2/c1-3-5(7)4(2)6/h3H2,1-2H3
    Key: TZMFJUDUGYTVRY-UHFFFAOYAL
  • CCC(=O)C(=O)C
Properties
C5H8O2
Molar mass 100.117 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Uses for acetylpropionyl include as a:

Food production facilities use acetylpropionyl in foods such as cookies, coffee, cereal, and chocolate.[4] It is also found in nicotine containing liquids for vaping, and in flavored cigarettes.[4] It is often used as a flavoring substitute for diacetyl, but may share similar human pulmonary toxicity.[5][6]

Safety

As a flavoring agent, it is an ingredient in some e-liquid products for use with electronic cigarettes to give a buttery or caramel flavor.[7] There is substantial evidence of the pulmonary toxicity of acetylpropionyl in animals.[4] Rats exposed to acetylpropionyl develop both fibrosis and necrosis of the respiratory tract.[4] Mice exposed to acetylpropionyl demonstrate more bronchial constriction in response to methacholine challenge.[4] It is also known to cause genetic changes in animal brains.[5]

Acetylpropionyl has been used as a substitute for the toxic flavoring chemical diacetyl.[4] However, in one flavoring manufacturing facility that substituted diacetyl for acetylpropionyl, abnormal lung function values were associated with total time spent in production areas.[4] An investigation by NIOSH in 2009 at a facility that used buttermilk flavoring containing acetylpropionyl demonstrated that workers had higher than average reports of shortness of breath, asthma, and restrictive type spirometry defects.[8] Another investigation by NIOSH in 2013 at a flavoring manufacturer that used acetylpropionyl revealed that those workers who spent the most time working with flavoring chemicals, including acetylpropionyl, were more likely to have abnormal lung function as detected by pulmonary function tests.[9]  

See also

References
  1. "2,3-Pentanedione".
  2. Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.doi:10.1002/14356007.a15_077
  3. "2,3-Pentanedione (Acetyl Propionyl)".
  4. Holden, Van K.; Hines, Stella E. (March 2016). "Update on flavoring-induced lung disease". Current Opinion in Pulmonary Medicine. 22 (2): 158–164. doi:10.1097/MCP.0000000000000250. ISSN 1070-5287. PMID 26761629. S2CID 23095196.
  5. "Flavorings-Related Lung Disease: Exposures to Flavoring Chemicals". The National Institute for Occupational Safety and Health (NIOSH). CDC. 2018-11-21. Retrieved 2020-04-05.
  6. Kreiss, Kathleen (August 2017). "Recognizing occupational effects of diacetyl: What can we learn from this history?". Toxicology. 388: 48–54. doi:10.1016/j.tox.2016.06.009. PMC 5323392. PMID 27326900.
  7. National Academies of Sciences, Engineering, and Medicine (2018). "Chapter 5: Toxicology of E-Cigarette Constituents". In Eaton, David L.; Kwan, Leslie Y.; Stratton, Kathleen (eds.). Public Health Consequences of E-Cigarettes. Washington, DC: National Academies Press. p. 175. doi:10.17226/24952. ISBN 978-0-309-46834-3. PMID 29894118.
  8. Day, Gregory A.; Cummings, Kristin J.; Kullman, Greg J. (November 2009). Report on an Investigation of Buttermilk Flavoring Exposures and Respiratory Health at a Bakery Mix Production Facility (PDF) (Report). CDC.
  9. Cummings, Kristin J.; Boylstein, Randy J.; Stanton, Marcia L.; Piacitelli, Chris A. (September 2013). An evaluation of respiratory health at a flavoring manufacturing facility -- Kentucky (PDF) (Report). CDC.
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