Acetylpropionyl

Acetylpropionyl

Names
IUPAC name 2,3-Pentanedione
Identifiers
CAS Number	600-14-6
3D model (Jmol)	Interactive image
ChemSpider	11254
ECHA InfoCard	100.009.078
PubChem	11747
InChI 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
SMILES CCC(=O)C(=O)C
Properties
Chemical formula	C5H8O2
Molar mass	100.12 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

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

Uses for acetylpropionyl include:

• a solvent for cellulose acetate, paints, inks, and lacquers,
• a starting material for dyes, pesticides, and drugs,
• and a flavor, with an odor described as "buttery, cheesy, sweet, nutty, fruity, creamy, caramel".^[3]

Safety

As a flavoring agent, it is a controversial^[4] ingredient in some e-liquid products for use with electronic cigarettes. According to the National Institute for Occupational Safety and Health , inhalation of acetylpropionyl causes respiratory tract epithelial damage and fibrosis to lungs in animal studies. It also causes genetic changes in the animals' brains.^[5] Acetylpropionyl was found to cause both intraluminal and intramural fibrotic airway lesions in rats.^[6] One study of the composition of 159 different e-liquid products, performed by Farsalinos et al., concluded that the use of acetylpropionyl and diacetyl in E-liquids represents an avoidable risk, and additionally that proper measures should be taken by E-liquid manufacturers and flavoring suppliers to eliminate these hazards from the products.^[7]

See also

• Diacetyl, a similar diketone

References

1. http://pubchem.ncbi.nlm.nih.gov/compound/2_3-pentanedione#section=Top
2. Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.doi:10.1002/14356007.a15_077
3. http://www.chemicalland21.com/lifescience/foco/2,3-PENTANEDIONE.htm
4. http://www.nicvape.com/blog/A-Very-Important-Message-from-NicVape
5. "CDC - Flavorings-Related Lung Disease: Exposures to Flavoring Chemicals - NIOSH Workplace Safety and Health Topic". www.cdc.gov. Retrieved 2015-10-22.
6. Morgan, D. L.; Jokinen, M. P.; Price, H. C.; Gwinn, W. M.; Palmer, S. M.; Flake, G. P. (2012). "Bronchial and bronchiolar fibrosis in rats exposed to 2,3-pentanedione vapors: Implications for bronchiolitis obliterans in humans". Toxicologic Pathology. 40 (3): 448–65. doi:10.1177/0192623311431946. PMID 22215510.
7. Farsalinos, Konstantinos (2014-08-20). "Evaluation of Electronic Cigarette Liquids and Aerosol for the Presence of Selected Inhalation Toxins". Nicotine and Tobacco Research. Oxford Journals. Retrieved 2015-04-06.