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
CAS Number	106-68-3  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:80946  Y
ChemSpider	215929
ECHA InfoCard	100.003.113
PubChem CID	246728
UNII	79173B4107  Y
CompTox Dashboard (EPA)	DTXSID3041954
InChI 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
SMILES CCCCCC(=O)CC
Properties
Chemical formula	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]
Solubility in water	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

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), ^[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]}

Uses

3-Octanone is used as a flavor and fragrance ingredient. ^{[11] [12] [13]}

See also

• Filbertone

References

1. "3-Octanone". Sigma-Aldrich.
2. NIOSH Pocket Guide to Chemical Hazards. "#0418". National Institute for Occupational Safety and Health (NIOSH).
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. 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: 192–195. 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