2-Undecanone

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]

2-Undecanone
Names
Preferred IUPAC name
Undecan-2-one
Other names
Methyl nonyl ketone (MNK)
Nonyl methyl ketone
Methyldecananone
2-Hendecanone
Undecanone
IBI-246
Identifiers
CAS Number
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.579
EC Number
  • 203-937-5
KEGG
PubChem CID
RTECS number
  • YQ2820000
UNII
InChI
  • InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3 Y
    Key: KYWIYKKSMDLRDC-UHFFFAOYSA-N Y
  • InChI=1/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
    Key: KYWIYKKSMDLRDC-UHFFFAOYAV
SMILES
  • O=C(CCCCCCCCC)C
Properties
Chemical formula
 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)
Solubility in water
 0.00179 g/100 mL (25 °C)
Hazards
GHS labelling:
Pictograms
Signal word
 Warning
Hazard statements
 H400
Precautionary statements
 P273, P391, P501
NFPA 704 (fire diamond)
1
2
Flash point 88 °C (190 °F; 361 K)
Safety data sheet (SDS) External MSDS
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).
Y verify (what is YN ?)
Infobox references

Uses

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

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

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
  • 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
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