2-Undecanone

Chemical compound From Wikipedia, the free encyclopedia

2-Undecanone, also known as methyl nonyl ketone and IBI-246, is an organic compound with the formula CH3C(O)C9H19. It is a colorless oil. 2-Undecanone 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]

Quick Facts Names, Identifiers ...
2-Undecanone
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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.579
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 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
  • O=C(CCCCCCCCC)C
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:
GHS09: Environmental hazard
Warning
H400
P273, P391, P501
NFPA 704 (fire diamond)
ThumbHealth 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).
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Uses

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. 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

References

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