2-Undecanone

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]

2-Undecanone

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
CAS Number	112-12-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17700 Y
ChEMBL	ChEMBL1236582
ChemSpider	7871 Y
DrugBank	DB08688 Y
ECHA InfoCard	100.003.579
EC Number	203-937-5
KEGG	C01875 Y
PubChem CID	8163
RTECS number	YQ2820000
UNII	YV5DSO8CY9 Y
CompTox Dashboard (EPA)	DTXSID2021943
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
SMILES O=C(CCCCCCCCC)C
Properties
Chemical formula	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)
Solubility in water	0.00179 g/100 mL (25 °C)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H400
Precautionary statements	P273, P391, P501
NFPA 704 (fire diamond)	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). Y verify (what is YN ?) Infobox references

Uses

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. 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

• Perfume allergy