2-Undecanone, also known as methyl nonyl ketone and IBI-246, is an oily organic

Organic chemistry

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

 liquid manufactured synthetically, but which can also be extracted from oil of rue

Rue

Rue is a genus of strongly scented evergreen subshrubs 20–60 cm tall, in the family Rutaceae, native to the Mediterranean region, Macaronesia and southwest Asia. There are perhaps 8 to 40 species in the genus...

. It is found naturally in banana

Banana

Banana is the common name for herbaceous plants of the genus Musa and for the fruit they produce. Bananas come in a variety of sizes and colors when ripe, including yellow, purple, and red....

s, clove

Clove

Cloves are the aromatic dried flower buds of a tree in the family Myrtaceae. Cloves are native to the Maluku islands in Indonesia and used as a spice in cuisines all over the world...

s, ginger

Ginger

Ginger is the rhizome of the plant Zingiber officinale, consumed as a delicacy, medicine, or spice. It lends its name to its genus and family . Other notable members of this plant family are turmeric, cardamom, and galangal....

, guava

Guava

Guavas are plants in the myrtle family genus Psidium , which contains about 100 species of tropical shrubs and small trees. They are native to Mexico, Central America, and northern South America...

, strawberries, wild-grown tomato

Tomato

The word "tomato" may refer to the plant or the edible, typically red, fruit which it bears. Originating in South America, the tomato was spread around the world following the Spanish colonization of the Americas, and its many varieties are now widely grown, often in greenhouses in cooler...

es, and the perennial Houttuynia cordata.

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

Insect repellent

An insect repellent is a substance applied to skin, clothing, or other surfaces which discourages insects from landing or climbing on that surface. There are also insect repellent products available based on sound production, particularly ultrasound...

 or animal repellent

Animal repellent

Animal repellents are products designed to keep certain animals away from objects, areas, people, plants, or other animals.-Overview:Repellents generally work by taking advantage of an animal's natural aversion to something, and often the thing chosen is something that the animal has learned to...

. Typically, 1–2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, aerosol spray

Aerosol spray

Aerosol spray is a type of dispensing system which creates an aerosol mist of liquid particles. This is used with a can or bottle that contains a liquid under pressure. When the container's valve is opened, the liquid is forced out of a small hole and emerges as an aerosol or mist...

, or gel.

Research from North Carolina State University has shown that it may be useful as a mosquito

Mosquito

Mosquitoes are members of a family of nematocerid flies: the Culicidae . The word Mosquito is from the Spanish and Portuguese for little fly...

 repellent, as effective as, or even more effective than, DEET

DEET

N,N-Diethyl-meta-toluamide, abbreviated DEET, is a slightly yellow oil. It is the most common active ingredient in insect repellents...

.

Chemical properties

2-Undecanone is a ketone

Ketone

In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

 that is soluble in ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...

, benzene

Benzene

Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

, chloroform

Chloroform

Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...

, and acetone

Acetone

Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

, but its large carbon chain renders it insoluble in water. Like most methyl ketone

Ketone

In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

s, 2-undecanone undergoes a haloform reaction

Haloform reaction

The haloform reaction is a chemical reaction where a haloform is produced by the exhaustive halogenation of a methyl ketone in the presence of a base. R may be , alkyl or aryl...

 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

Chloroform

Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...

, and sodium hydroxide.

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