2-Undecanone

2-Undecanone
IUPAC name Undecan-2-one
Other names Methyl nonyl ketone (MNK) Nonyl methyl ketone Methyldecananone 2-Hendecanone Undecanone IBI-246
Identifiers
CAS number	112-12-9 Y
ChemSpider	7871 Y
UNII	YV5DSO8CY9 Y
DrugBank	DB08688
KEGG	C01875 Y
ChEBI	CHEBI:17700 Y
RTECS number	YQ2820000
Jmol-3D images	Image 1
SMILES O=C(CCCCCCCCC)C
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
Properties
Molecular formula	C11H22O
Molar mass	170.29 g mol−1
Appearance	Colorless or pale yellow liquid
Density	0.829 g/cm³, liquid
Melting point	15 °C, 288 K, 59 °F
Boiling point	231 °C, 504 K, 448 °F
Solubility in water	0.00179 g/100 mL (25 °C)
Hazards
MSDS	External MSDS
EU classification	Flammable (F) Irritant (Xi)
R-phrases	R50 R51
S-phrases	S23 S24 S25
NFPA 704	2 1 0
Flash point	88 °C
Related compounds
Related Ketones	Acetone Butan-2-one 3-pentanone
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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, 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 base and hypochlorite (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

• Perfume allergy

Notes

1. ^ Liang, Minmin et al.; Qi, M; Zhang, C; Zhou, S; Fu, R; Huang, J (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. 12. http://ipm.ncsu.edu/current_ipm/Broadcasts/broadcast06-02b.html. 

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