2-Undecanone

2-Undecanone 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, and strawberries. 2-Undecanone is used in the perfumery and flavoring industries, but because of its strong odor it is primarily used as an insect or animal repellant. Typically, 1–2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, aerosol spray, or gel.

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2-Undecanone is a ketone, also known as methyl nonyl ketone (MNK). It 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. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide.

CH₃CO(CH₂)₈CH₃ + 3NaOCl → CH₃(CH₂)₈COONa + CHCl₃ + 2NaOH

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
• http://www.thegoodscentscompany.com/data/rw1021151.html