Perilla ketone

Perilla ketone

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Names
IUPAC name 1-(3-Furanyl)-4-methyl-1-pentanone
Other names beta-Furyl isoamyl ketone
Identifiers
CAS Number	553-84-4 Y
Jmol 3D model	Interactive image
PubChem	68381
SMILES CC(C)CCC(C1=COC=C1)=O
Properties
Chemical formula	C10H14O2
Molar mass	166.22 g·mol−1
Appearance	Liquid
Density	0.9920 g/cm³
Melting point	<25 °C
Boiling point	196 °C (385 °F; 469 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Perilla ketone is a natural terpenoid that consists of a furan ring with a six-carbon side chain containing a ketone functional group. It is a colorless oil that is sensitive to oxygen, becoming colored upon standing. The ketone was identified in 1943 by Sebe as the main component of the essential oil of Perilla frutescens. Perilla ketone is present in the leaves and seeds of purple mint (Perilla frutescens), which is toxic to some animals. When cattle and horses consume purple mint when grazing in fields in which it grows, the perilla ketone causes pulmonary edema leading to a condition sometimes called perilla mint toxicosis.

Synthesis

Perilla ketone was synthesized in 1957 by Matsuura from 3-furoyl chloride and an organocadmium compound similar to the Gilman reagent made from an isoamyl Grignard reagent and cadmium chloride. Perilla ketone (3-Furyl isoamyl ketone) has been prepared in 74% yield via the Stille reaction from a 3-furyl-organotin compound and isocaproyl chloride in tetrahydrofuran solvent.

See also

• Perillene