Perilla ketone

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Perilla ketone
Perilla ketone.svg
Names
IUPAC name
1-(3-Furanyl)-4-methyl-1-pentanone
Other names
beta-Furyl isoamyl ketone
Identifiers
3D model (Jmol)
Properties
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 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.[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[edit]

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[edit]

References[edit]

  1. ^ Vittorio Farina (1943). "Perilla ketone". Nippon Kagaku Kaishi. 64: 1130–6. 
  2. ^ a b Perilla: Botany, Uses and Genetic Resources
  3. ^ Teruo Matsuura (1957). "Natural furan derivatives. I. The synthesis of perilla ketone". Bulletin of the Chemical Society of Japan. 30: 430–1. doi:10.1246/bcsj.30.430. 
  4. ^ Vittorio Farina; Krishnamurthy, Venkat; Scott, William J. (1997). "The Stille reaction". Organic Reactions (Hoboken, NJ, United States). 50.