3-Octanone

3-Octanone
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
ChEMBL
ChemSpider
ECHA InfoCard 100.003.113 Edit this at Wikidata
EC Number
  • 203-423-0
KEGG
UNII
UN number 2271
  • InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3
    Key: RHLVCLIPMVJYKS-UHFFFAOYSA-N
  • InChI=1/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3
    Key: RHLVCLIPMVJYKS-UHFFFAOYAV
  • CCCCCC(=O)CC
Properties
C8H16O
Molar mass 128.215 g·mol−1
Appearance colorless liquid
Density 0.822 g/mL
Boiling point 167 to 168 °C (333 to 334 °F; 440 to 441 K)
insoluble in water
Vapor pressure 2 mmHg (20°C)
Hazards
Flash point 59 °C; 138 °F; 332 K
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 25 ppm (130 mg/m3)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3-Octanone is an organic compound with the formula C5H11C(O)C2H5. 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), herbs (such as rosemary, basil, and thyme), and nectarines. It was also found to be present in Japanese catnip (Schizonepeta tenuifolia) and the pine king bolete (Boletus pinophilus). It is produced by oyster mushrooms as an nematicide to kill roundworms.

Uses

3-Octanone is used as a flavor and fragrance ingredient.

See also

References

  1. 1 2 "3-Octanone". Sigma-Aldrich.
  2. 1 2 3 "#0418". NIOSH Pocket Guide to Chemical Hazards. National Institute for Occupational Safety and Health.
  3. ↑ Opdyke, D.L.J., ed. (1979). Monographs on Fragrance Raw Materials. New York: Pergamon Press. p. 346.
  4. ↑ Koedam, A.; et al. (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. S2CID 87276514.
  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; et al. (1988). "Nectarine volatiles: vacuum steam distillation versus headspace sampling". J Agric Food Chem. 36 (3): 553–560. Bibcode:1988JAFC...36..553T. 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. PMC 3210999. 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 (1): 192–195. Bibcode:2015NBHAC..43..192B. doi:10.15835/nbha4319731.
  9. ↑ Li, Huiping; Liu, Junjie; Hou, Ziqiang; Luo, Xin; Lin, Jinsheng; Jiang, Ning; Hou, Lijuan; Ma, Lin; Li, Cuixin; Qu, Shaoxuan (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. S2CID 250931270.
  10. ↑ Ouellette, Jennifer (18 January 2023). "Carnivorous oyster mushrooms can kill roundworms with "nerve gas in a lollipop"". Ars Technica. Retrieved 26 January 2023.
  11. ↑ "3-octanone". thegoodscentscompany.com.
  12. ↑ Ashford RD (1994). Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd. p. 389.
  13. ↑ Code of Federal Regulations Title 21