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.
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| Names | |
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| 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
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.113 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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)
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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).
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Occurrence
edit3-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
edit3-Octanone is used as a flavor and fragrance ingredient.[12][13][14]
See also
editReferences
edit- ^ a b "3-Octanone". Sigma-Aldrich.
- ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0418". National Institute for Occupational Safety and Health (NIOSH).
- ^ Opdyke, D.L.J., ed. (1979). Monographs on Fragrance Raw Materials. New York: Pergamon Press. p. 346.
- ^ 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 87276514.1–2&rft.pages=144&rft.date=1978&rft_id=info:doi/10.1515/znc-1978-1-226&rft_id=https://api.semanticscholar.org/CorpusID:87276514#id-name=S2CID&rft.au=Koedam, A.&rft_id=https://doi.org/10.1515%2Fznc-1978-1-226&rfr_id=info:sid/en.wikipedia.org:3-Octanone" class="Z3988">
- ^ 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.2004.05.056.131-137&rft.date=2005&rft_id=info:doi/10.1016/j.foodchem.2004.05.056&rft.aulast=Lee&rft.aufirst=Seung-Joo&rft.au=Umano, Katumi&rft.au=Shibamoto, Takayuki&rft.au=Lee, Kwang-Geun&rfr_id=info:sid/en.wikipedia.org:3-Octanone" class="Z3988">
- ^ Takeoka GR; et al. (1988). "Nectarine volatiles: vacuum steam distillation versus headspace sampling". J Agric Food Chem. 36 (3): 553–560. doi:10.1021/jf00081a037.553-560&rft.date=1988&rft_id=info:doi/10.1021/jf00081a037&rft.au=Takeoka GR&rfr_id=info:sid/en.wikipedia.org:3-Octanone" class="Z3988">
- ^ 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 22072908.6635-44&rft.date=2011&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3210999#id-name=PMC&rft_id=info:pmid/22072908&rft_id=info:doi/10.3390/ijms12106635&rft.aulast=Yu&rft.aufirst=S&rft.au=Chen, Y&rft.au=Zhang, L&rft.au=Shan, M&rft.au=Tang, Y&rft.au=Ding, A&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3210999&rfr_id=info:sid/en.wikipedia.org:3-Octanone" class="Z3988">
- ^ 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/nbha4319731.192-195&rft.date=2015&rft_id=info:doi/10.15835/nbha4319731&rft.aulast=Bozok&rft.aufirst=Fuat&rft.au=Zarifikhosroshahi, Mozhgan&rft.au=Kafkas, Ebru&rft.au=Taşkin, Hatira&rft.au=Buyukalaca, Saadet&rft_id=https://doi.org/10.15835%2Fnbha4319731&rfr_id=info:sid/en.wikipedia.org:3-Octanone" class="Z3988">
- ^ 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.
- ^ 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.
- ^ Ouellette, Jennifer (18 January 2023). "Carnivorous oyster mushrooms can kill roundworms with "nerve gas in a lollipop"". Ars Technica. Retrieved 26 January 2023.
- ^ "3-octanone". thegoodscentscompany.com.
- ^ Ashford RD (1994). Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd. p. 389.
- ^ Code of Federal Regulations Title 21