2-Undecanone
| 2-Undecanone | |
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Undecan-2-one |
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Other names
Methyl nonyl ketone (MNK) |
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| Identifiers | |
| CAS number | 112-12-9  |
| ChemSpider | 7871 |
| UNII | YV5DSO8CY9 |
| DrugBank | DB08688 |
| KEGG | C01875 |
| ChEBI | CHEBI:17700 |
| RTECS number | YQ2820000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C11H22O |
| Molar mass | 170.29 g mol−1 |
| Appearance | Colorless or pale yellow liquid |
| Density | 0.829 g/cm³, liquid |
| Melting point |
15 °C, 288 K, 59 °F |
| Boiling point |
231 °C, 504 K, 448 °F |
| Solubility in water | 0.00179 g/100 mL (25 °C) |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Flammable (F) Irritant (Xi) |
| R-phrases | R50 R51 |
| S-phrases | S23 S24 S25 |
| NFPA 704 |
 2
1
0
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| Flash point | 88 °C |
| Related compounds | |
| Related Ketones | Acetone Butan-2-one 3-pentanone |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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]
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[edit] 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]
[edit] 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 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
[edit] See also
[edit] Notes
- ^ Liang, Minmin et al.; Qi, M; Zhang, C; Zhou, S; Fu, R; Huang, J (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.
- ^ 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. http://ipm.ncsu.edu/current_ipm/Broadcasts/broadcast06-02b.html.
[edit] 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
