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2-Undecanone

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This is an old revision of this page, as edited by JWBE (talk | contribs) at 12:12, 9 September 2018 (removed Category:Dialkylketones; added Category:Alkanones using HotCat). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

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
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.579 Edit this at Wikidata
EC Number
  • 203-937-5
KEGG
RTECS number
  • YQ2820000
UNII
  • InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3 checkY
    Key: KYWIYKKSMDLRDC-UHFFFAOYSA-N checkY
  • InChI=1/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
    Key: KYWIYKKSMDLRDC-UHFFFAOYAV
  • O=C(CCCCCCCCC)C
Properties
C11H22O
Molar mass 170.296 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
GHS labelling:
GHS09: Environmental hazard
Warning
H400
P273, P391, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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 fuelInstability (yellow): no hazard codeSpecial hazards (white): no code
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).
checkY verify (what is checkY☒N ?)

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

  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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