3-Octanone
{{Chembox
| ImageFile = 3-Octanone.svg
| ImageSize = 200px
| PIN = Octan-3-one
| OtherNames = Ethyl amyl ketone; n-Octanone-3; Amyl ethyl ketone; Ethyl pentyl ketone; Ethyl n-amyl ketone; Ethyl n-pentyl ketone
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 106-68-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 79173B4107
| PubChem = 246728
| ChemSpiderID = 215929
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 80946
| SMILES = CCCCCC(=O)CC
| InChI = 1/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3
| InChIKey = RHLVCLIPMVJYKS-UHFFFAOYAV
| StdInChI = 1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3
| StdInChIKey = RHLVCLIPMVJYKS-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=8 | H=16 | O=1
| Appearance = colorless liquid
| Density = 0.822 g/mL{{Cite web | url = http://www.sigmaaldrich.com/catalog/product/aldrich/136913?lang=en | publisher = Sigma-Aldrich | title = 3-Octanone}}
| MeltingPt =
| BoilingPtC = 167 to 168
| Solubility = insoluble in water{{PGCH|0418}}
| VaporPressure = 2 mmHg (20°C)
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| AutoignitionPt =
| PEL = TWA 25 ppm (130 mg/m3)
}}
}}
3-Octanone is an organic compound with the formula {{chem2|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),{{cite book | editor = Opdyke, D.L.J. | title = Monographs on Fragrance Raw Materials | location = New York | publisher = Pergamon Press | date = 1979 | page = 346}} herbs (such as rosemary,{{cite journal | title = Freshly Distilled Oil of the Leaves of Rasmarinus Officianalis L Contained 3-Octanone | author = Koedam, A. | journal = Z. Naturforsch. C | volume =33C | issue = 1–2 | pages = 144 | date = 1978| doi = 10.1515/znc-1978-1-226 | s2cid = 87276514 |display-authors=etal| doi-access = free }} basil, and thyme{{cite journal |doi=10.1016/j.foodchem.2004.05.056|title=Identification of volatile components in basil (Ocimum basilicum L.) and thyme leaves (Thymus vulgaris L.) and their antioxidant properties |year=2005 |last1=Lee |first1=Seung-Joo |last2=Umano |first2=Katumi |last3=Shibamoto |first3=Takayuki |last4=Lee |first4=Kwang-Geun |journal=Food Chemistry |volume=91 |pages=131–137 }}), and nectarines.{{cite journal |title=Nectarine volatiles: vacuum steam distillation versus headspace sampling| author = Takeoka GR | journal = J Agric Food Chem | volume = 36 |issue=3| pages = 553–560 | date = 1988|doi=10.1021/jf00081a037 |display-authors=etal}} It was also found to be present in Japanese catnip (Schizonepeta tenuifolia){{Cite journal
| pmid = 22072908
| year = 2011
| last1 = Yu
| first1 = S
| title = Quantitative Comparative Analysis of the Bio-Active and Toxic Constituents of Leaves and Spikes of Schizonepeta tenuifolia at Different Harvesting Times
| journal = International Journal of Molecular Sciences
| volume = 12
| issue = 10
| pages = 6635–44
| last2 = Chen
| first2 = Y
| last3 = Zhang
| first3 = L
| last4 = Shan
| first4 = M
| last5 = Tang
| first5 = Y
| last6 = Ding
| first6 = A
| doi = 10.3390/ijms12106635
| pmc = 3210999
| doi-access = free
}} and the pine king bolete (Boletus pinophilus).{{cite journal |doi=10.15835/nbha4319731|title=Comparison of Volatile Compounds of Fresh Boletus edulis and B. Pinophilus in Marmara Region of Turkey|year=2015|last1=Bozok|first1=Fuat|last2=Zarifikhosroshahi|first2=Mozhgan|last3=Kafkas|first3=Ebru|last4=Taşkin|first4=Hatira|last5=Buyukalaca|first5=Saadet|journal=Notulae Botanicae Horti Agrobotanici Cluj-Napoca|volume=43|pages=192–195|doi-access=free}} It is produced by oyster mushrooms as an insecticide to kill roundworms.{{cite journal |doi=10.1016/j.foodres.2022.111708|title=Activation of mycelial defense mechanisms in the oyster mushroom Pleurotus ostreatus induced by Tyrophagus putrescentiae |year=2022 |last1=Li |first1=Huiping |last2=Liu |first2=Junjie |last3=Hou |first3=Ziqiang |last4=Luo |first4=Xin |last5=Lin |first5=Jinsheng |last6=Jiang |first6=Ning |last7=Hou |first7=Lijuan |last8=Ma |first8=Lin |last9=Li |first9=Cuixin |last10=Qu |first10=Shaoxuan |journal=Food Research International |volume=160 |page=111708 |pmid=36076457 |s2cid=250931270 }}{{cite journal |doi=10.1016/j.foodres.2022.111708|title=Activation of mycelial defense mechanisms in the oyster mushroom Pleurotus ostreatus induced by Tyrophagus putrescentiae |year=2022 |last1=Li |first1=Huiping |last2=Liu |first2=Junjie |last3=Hou |first3=Ziqiang |last4=Luo |first4=Xin |last5=Lin |first5=Jinsheng |last6=Jiang |first6=Ning |last7=Hou |first7=Lijuan |last8=Ma |first8=Lin |last9=Li |first9=Cuixin |last10=Qu |first10=Shaoxuan |journal=Food Research International |volume=160 |page=111708 |pmid=36076457 |s2cid=250931270 }}{{cite web |last1=Ouellette |first1=Jennifer |title=Carnivorous oyster mushrooms can kill roundworms with "nerve gas in a lollipop" |url=https://arstechnica.com/science/2023/01/carnivorous-oyster-mushrooms-can-kill-roundworms-with-nerve-gas-in-a-lollipop/?comments=1&comments-page=1 |website=Ars Technica |access-date=26 January 2023 |language=en-us |date=18 January 2023}}
Uses
3-Octanone is used as a flavor and fragrance ingredient.{{cite web | url = http://www.thegoodscentscompany.com/data/rw1004231.html | title = 3-octanone | publisher = thegoodscentscompany.com}}{{cite book | author = Ashford RD | title = Ashford's Dictionary of Industrial Chemicals | publisher = Wavelength Publications Ltd | location = London, England | page = 389 | date = 1994}}[http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?FR=172.515 Code of Federal Regulations Title 21]