2-Undecanone
2-Undecanone | |
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Undecan-2-one | |
Other names Methyl nonyl ketone (MNK) | |
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; 59 °F; 288 K |
Boiling point | 231 °C; 448 °F; 504 K |
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
|
Flash point | 88 °C; 190 °F; 361 K |
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 (77 °F), 100 kPa) | |
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]
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 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 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". Pesticide Broadcast 12 (5).
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