Chemistry:3-Octanone

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3-Octanone
3-Octanone.svg
Names
Preferred IUPAC name
Octan-3-one
Other names
Ethyl amyl ketone; n-Octanone-3; Amyl ethyl ketone; Ethyl pentyl ketone; Ethyl n-amyl ketone; Ethyl n-pentyl ketone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
Properties
C8H16O
Molar mass 128.215 g·mol−1
Appearance colorless liquid
Density 0.822 g/mL[1]
Boiling point 167 to 168 °C (333 to 334 °F; 440 to 441 K)[1]
insoluble in water[2]
Vapor pressure 2 mmHg (20°C)[2]
Hazards
Flash point 59 °C; 138 °F; 332 K
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 25 ppm (130 mg/m3)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

3-Octanone is an organic compound with the formula C
5H
11C(O)C
2H
5. A colorless fragrant liquid, it is classified as a ketone. It is one of three octanones, the others being 2-octanone and 4-octanone.

Occurrence

3-Octanone is found in a variety of sources such as plants (such as lavender),[3] herbs (such as rosemary,[4] basil, and thyme[5]), and nectarines.[6] It was also found to be present in Japanese catnip (Schizonepeta tenuifolia)[7] and the pine king bolete (Boletus pinophilus).[8] It is produced by oyster mushrooms as an insecticide to kill roundworms.[9][10][11]

Uses

3-Octanone is used as a flavor and fragrance ingredient.[12][13][14]

See also

References

  1. ↑ 1.0 1.1 "3-Octanone". Sigma-Aldrich. http://www.sigmaaldrich.com/catalog/product/aldrich/136913?lang=en. 
  2. ↑ 2.0 2.1 2.2 2.3 NIOSH Pocket Guide to Chemical Hazards. "#0418". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0418.html. 
  3. ↑ Opdyke, D.L.J., ed (1979). Monographs on Fragrance Raw Materials. New York: Pergamon Press. p. 346. 
  4. ↑ Koedam, A. (1978). "Freshly Distilled Oil of the Leaves of Rasmarinus Officianalis L Contained 3-Octanone". Z. Naturforsch. C 33C (1–2): 144. doi:10.1515/znc-1978-1-226. 
  5. ↑ Lee, Seung-Joo; Umano, Katumi; Shibamoto, Takayuki; Lee, Kwang-Geun (2005). "Identification of volatile components in basil (Ocimum basilicum L.) and thyme leaves (Thymus vulgaris L.) and their antioxidant properties". Food Chemistry 91: 131–137. doi:10.1016/j.foodchem.2004.05.056. 
  6. ↑ Takeoka GR (1988). "Nectarine volatiles: vacuum steam distillation versus headspace sampling". J Agric Food Chem 36 (3): 553–560. doi:10.1021/jf00081a037. 
  7. ↑ Yu, S; Chen, Y; Zhang, L; Shan, M; Tang, Y; Ding, A (2011). "Quantitative Comparative Analysis of the Bio-Active and Toxic Constituents of Leaves and Spikes of Schizonepeta tenuifolia at Different Harvesting Times". International Journal of Molecular Sciences 12 (10): 6635–44. doi:10.3390/ijms12106635. PMID 22072908. 
  8. ↑ Bozok, Fuat; Zarifikhosroshahi, Mozhgan; Kafkas, Ebru; Taşkin, Hatira; Buyukalaca, Saadet (2015). "Comparison of Volatile Compounds of Fresh Boletus edulis and B. Pinophilus in Marmara Region of Turkey". Notulae Botanicae Horti Agrobotanici Cluj-Napoca 43: 192–195. doi:10.15835/nbha4319731. 
  9. ↑ Li, Huiping; Liu, Junjie; Hou, Ziqiang; Luo, Xin; Lin, Jinsheng; Jiang, Ning; Hou, Lijuan; Ma, Lin et al. (2022). "Activation of mycelial defense mechanisms in the oyster mushroom Pleurotus ostreatus induced by Tyrophagus putrescentiae". Food Research International 160: 111708. doi:10.1016/j.foodres.2022.111708. PMID 36076457. 
  10. ↑ Li, Huiping; Liu, Junjie; Hou, Ziqiang; Luo, Xin; Lin, Jinsheng; Jiang, Ning; Hou, Lijuan; Ma, Lin et al. (2022). "Activation of mycelial defense mechanisms in the oyster mushroom Pleurotus ostreatus induced by Tyrophagus putrescentiae". Food Research International 160: 111708. doi:10.1016/j.foodres.2022.111708. PMID 36076457. 
  11. ↑ Ouellette, Jennifer (18 January 2023). "Carnivorous oyster mushrooms can kill roundworms with "nerve gas in a lollipop"" (in en-us). https://arstechnica.com/science/2023/01/carnivorous-oyster-mushrooms-can-kill-roundworms-with-nerve-gas-in-a-lollipop/?comments=1&comments-page=1. 
  12. ↑ "3-octanone". thegoodscentscompany.com. http://www.thegoodscentscompany.com/data/rw1004231.html. 
  13. ↑ Ashford RD (1994). Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd. p. 389. 
  14. ↑ Code of Federal Regulations Title 21



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