Perilla ketone

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]

Perilla ketone

Names
Preferred IUPAC name 1-(Furan-3-yl)-4-methylpentan-1-one
Other names beta-Furyl isoamyl ketone
Identifiers
CAS Number	553-84-4 Y
3D model (JSmol)	Interactive image
ChemSpider	61667
PubChem CID	68381
UNII	CV69S6Y94V Y
CompTox Dashboard (EPA)	DTXSID10203828
InChI InChI=LVHLZMUFIYAEQB-UHFFFAOYSA-N
SMILES CC(C)CCC(C1=COC=C1)=O
Properties
Chemical formula	C10H14O2
Molar mass	166.217
Appearance	Liquid
Density	0.9920 g/cm3
Melting point	<25 °C
Boiling point	196 °C (385 °F; 469 K)
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

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 has also 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