2-Undecanone

2-Undecanone
Names
IUPAC name
Undecan-2-one
Other names
Methyl nonyl ketone (MNK)
Nonyl methyl ketone
Methyldecananone
2-Hendecanone
Undecanone
IBI-246
Identifiers
112-12-9 YesY
ChEBI CHEBI:17700 YesY
ChemSpider 7871 YesY
DrugBank DB08688 YesY
Jmol interactive 3D Image
KEGG C01875 YesY
RTECS number YQ2820000
UNII YV5DSO8CY9 YesY
Properties
C11H22O
Molar mass 170.30 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
Safety data sheet External MSDS
Flammable (F)
Irritant (Xi)
R-phrases R50 R51
S-phrases S23 S24 S25
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
2
1
Flash point 88 °C (190 °F; 361 K)
Related compounds
Related Ketones
Acetone
Butan-2-one
3-pentanone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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]

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, 12% 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

  1. 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.
  2. Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET, Science Daily, June 2002
  3. Stephen J. Toth, Jr. and Wayne G. Buhler (2002). "North Carolina State University Scientist Discovers Mosquito Repellent in Tomatoes". Pesticide Broadcast 12 (5).

References

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