Perilla ketone

Perilla ketone

Names
IUPAC name 1-(3-Furanyl)-4-methyl-1-pentanone
Other names beta-Furyl isoamyl ketone
Identifiers
CAS Registry Number	553-84-4
Jmol-3D images	Image
PubChem	68381
SMILES CC(C)CCC(C1=COC=C1)=O
Properties
Molecular 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)
Except where noted otherwise, data is 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.^[1] Perilla ketone is present in the leaves and seeds of purple mint (Perilla frutescens), which is toxic to some animals.^[2] 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.^[2]

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.^[3] 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.^[4]

See also

• Perillene

References