3-Octanone

3-Octanone
	source ↗
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;
ChEMBL	ChEMBL2269087;
ChemSpider	215929;
ECHA InfoCard	100.003.113
EC Number	203-423-0;
KEGG	C17145;
PubChem CID	246728;
UNII	79173B4107 Y;
UN number	2271
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
Boiling point	167 to 168 °C (333 to 334 °F; 440 to 441 K)
Solubility in water	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). 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 thyme⁵), 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 nematicide to kill roundworms.⁹¹⁰

Uses

3-Octanone is used as a flavor and fragrance ingredient.¹¹¹²¹³

References

"3-Octanone". Sigma-Aldrich.
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.
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.
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.
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.
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.
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

[Aldrich-1] "3-Octanone". Sigma-Aldrich.

[NIOSH-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. 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.

[bozok-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.

[Shrooms-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

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References