2-Undecanone
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| Names | |
|---|---|
| IUPAC name
Undecan-2-one
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| Other names
Methyl nonyl ketone (MNK)
Nonyl methyl ketone Methyldecananone 2-Hendecanone Undecanone IBI-246 | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.579 |
| KEGG | |
| RTECS number |
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CompTox Dashboard (EPA)
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| Properties | |
| C11H22O | |
| Molar mass | 170.296 g·mol−1 |
| Appearance | Colorless or pale yellow liquid |
| Density | 0.829 g/cm³, liquid |
| Melting point | 15 °C (59 °F; 288 K) |
| Boiling point | 231 °C (448 °F; 504 K) |
| 0.00179 g/100 mL (25 °C) | |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | 88 °C |
| Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Undecanone, also known as methyl nonyl ketone and IBI-246, is an oily organic liquid manufactured synthetically, but which can also be extracted from oil of rue. It is found naturally in bananas, cloves, ginger, guava, strawberries, wild-grown tomatoes, and the perennial Houttuynia cordata.[1]
Uses
2-Undecanone is used in the perfumery and flavoring industries, but 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.
Research from North Carolina State University has shown that it may be useful as a mosquito repellent, as effective as, or even more effective than, DEET.[2][3]
Chemical properties
2-Undecanone is a ketone that is soluble in ethanol, benzene, chloroform, and acetone, but its large carbon chain renders it insoluble in water. Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a base and hypochlorite (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
- ^ Liang, Minmin; Qi, M; Zhang, C; Zhou, S; Fu, R; Huang, J; et al. (2005). "Gas chromatography–mass spectrometry analysis of volatile compounds from Houttuynia cordata Thunb after extraction by solid-phase microextraction, flash evaporation and steam distillation". Analytica Chimica Acta. 531 (1): 97–104. doi:10.1016/j.aca.2004.09.082.
{{cite journal}}:|access-date=requires|url=(help); Cite has empty unknown parameter:|coauthors=(help); Explicit use of et al. in:|first=(help) - ^ Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET, Science Daily, June 2002
- ^ Stephen J. Toth, Jr. and Wayne G. Buhler (2002). "North Carolina State University Scientist Discovers Mosquito Repellent in Tomatoes". 12 (5).
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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
- 2-Undecanone from The Good Scents Company
- MSDS for 2-Undecanone