2-Undecanone
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| Names | |
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| Preferred IUPAC name
Undecan-2-one | |
| Other names
Methyl nonyl ketone (MNK)
Nonyl methyl ketone Methyldecananone 2-Hendecanone Undecanone IBI-246 | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
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| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.003.579 |
| EC Number |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C11H22O | |
| Molar mass | 170.296 g·mol−1 |
| Appearance | Colorless 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 | |
| GHS labelling: | |
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| Warning | |
| H400 | |
| P273, P391, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 88 °C (190 °F; 361 K) |
| Safety data sheet (SDS) | External MSDS |
| Related compounds | |
Related Ketones
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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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2-Undecanone, also known as methyl nonyl ketone and IBI-246, is the organic compound with the formula CH3C(O)C9H19. It a colorless oil. It 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.[1]
Uses
[edit]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.[2][3]
Chemical properties
[edit]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
[edit]Notes
[edit]- ^ 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. Bibcode:2005AcAC..531...97L. doi:10.1016/j.aca.2004.09.082. Archived from the original on 2020-09-14. Retrieved 2024-02-02.
- ^ Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET Archived 2023-09-28 at the Wayback Machine, 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). Archived from the original on 2008-05-13. Retrieved 2009-01-24.
References
[edit]- 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[permanent dead link]