2-Undecanone
{{chembox
| Watchedfields = changed
| verifiedrevid = 477215677
| Name = 2-Undecanone
| ImageFile = 2-undecanone.svg
| ImageName = 2-undecanone
| PIN = Undecan-2-one
| OtherNames = Methyl nonyl ketone (MNK)
Nonyl methyl ketone
Methyldecananone
2-Hendecanone
Undecanone
IBI-246
|Section1={{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17700
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YV5DSO8CY9
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB08688
| SMILES = O=C(CCCCCCCCC)C
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7871
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01875
| PubChem = 8163
| EC_number = 203-937-5
| ChEMBL = 1236582
| 3DMet = B00364
| InChI = 1/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
| InChIKey = KYWIYKKSMDLRDC-UHFFFAOYAV
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KYWIYKKSMDLRDC-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 112-12-9
| RTECS = YQ2820000
}}
|Section2={{Chembox Properties
| C=11 | H=22 | O=1
| Appearance = Colorless liquid
| Density = 0.829 g/cm3, liquid
| Solubility = 0.00179 g/100 mL (25 °C)
| MeltingPtC = 15
| BoilingPtC = 231
}}
|Section7={{Chembox Hazards
| ExternalSDS = [http://msds.chem.ox.ac.uk/UN/2-undecanone.html External MSDS]
| NFPA-H = 1
| NFPA-F = 2
| NFPA-R =
| GHSPictograms = {{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|400}}
| PPhrases = {{P-phrases|273|391|501}}
| FlashPtC = 88
}}
|Section8={{Chembox Related
| OtherFunction_label = Ketones
| OtherFunction = Acetone
Butan-2-one
3-pentanone
}}
}}
2-Undecanone, also known as methyl nonyl ketone and IBI-246, is an organic compound with the formula CH3C(O)C9H19. It is a colorless oil. 2-Undecanone is usually produced synthetically, but it can also be extracted from various plant sources, including from essential oil of rue. It is found naturally in bananas, cloves, ginger, guava, strawberries, wild-grown tomatoes, and the perennial leaf vegetable Houttuynia cordata.{{cite journal
| last1 = Liang
| first1 = Minmin
| last2 = Qi
| first2 = M
| last3 = Zhang
| first3 = C
| last4 = Zhou
| first4 = S
| last5 = Fu
| first5 = R
| last6 = Huang
| first6 = J
| title = Gas chromatography–mass spectrometry analysis of volatile compounds from Houttuynia cordata Thunb after extraction by solid-phase microextraction, flash evaporation and steam distillation
| journal = Analytica Chimica Acta
| volume = 531
| issue = 1
| pages = 97–104
| year = 2005
| url = http://ir.rcees.ac.cn/handle/311016/23180
| doi = 10.1016/j.aca.2004.09.082
| bibcode = 2005AcAC..531...97L
| display-authors = etal
| access-date = 2024-02-02
| archive-date = 2020-09-14
| archive-url = https://web.archive.org/web/20200914184859/http://ir.rcees.ac.cn/handle/311016/23180
| url-status = dead
}}
Uses
Because of its strong odor it is primarily used as an insect repellent or animal repellent. Typically, 1–2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, aerosol spray, or gel. 2-Undecanone is also used in the perfumery and flavoring industries.
It has been investigated as a mosquito repellant, like DEET.[https://www.sciencedaily.com/releases/2002/06/020611070622.htm Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET] {{Webarchive|url=https://web.archive.org/web/20230928005519/https://www.sciencedaily.com/releases/2002/06/020611070622.htm |date=2023-09-28 }}, Science Daily, June 2002{{cite journal | journal = Pesticide Broadcast | author = Stephen J. Toth, Jr. and Wayne G. Buhler | volume = 12 | issue = 5 | year = 2002 | title = North Carolina State University Scientist Discovers Mosquito Repellent in Tomatoes | url = http://ipm.ncsu.edu/current_ipm/Broadcasts/broadcast06-02b.html | access-date = 2009-01-24 | archive-date = 2008-05-13 | archive-url = https://web.archive.org/web/20080513030943/http://ipm.ncsu.edu/current_ipm/Broadcasts/broadcast06-02b.html | url-status = live }}
Chemical properties
2-Undecanone is a ketone that is soluble in organic solvents but insoluble in water. Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a basic solution of hypochlorite. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide.
:CH3CO(CH2)8CH3 + 3 NaOCl → CH3(CH2)8COONa + CHCl3 + 2 NaOH
See also
Notes
{{reflist}}
References
- Lange's Handbook of Chemistry (14th Edition), McGraw-Hill, 1992; Section 1; Table 1.15
- The Condensed Chemical Dictionary (10th Edition), Gesner G. Hawley
- [http://www.thegoodscentscompany.com/data/rw1021151.html 2-Undecanone] from The Good Scents Company
- [http://www.albochem.com/wps/wp-content/2009/01/mnkmsds.pdf MSDS for 2-Undecanone]{{Dead link|date=March 2019 |bot=InternetArchiveBot |fix-attempted=yes }}
{{DEFAULTSORT:Undecanone, 2-}}