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
IUPAC name
1-(3-Furanyl)-4-methyl-1-pentanone
Other names
beta-Furyl isoamyl ketone
Identifiers
3D model (JSmol)
ChemSpider
UNII
Properties
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).
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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 (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]

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See also

References
  1. Sebe, Yeigai (1943). "Supplemental experiments on perilla ketone". Nippon Kagaku Kaishi (in Japanese). 64 (8): 1130–6. doi:10.1246/nikkashi1921.64.1130.
  2. Perilla: Botany, Uses and Genetic Resources
  3. Matsuura, Teruo (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. Farina, Vittorio; Krishnamurthy, Venkat; Scott, William J. (1997). "The Stille reaction". Organic Reactions. 50: 1–652. doi:10.1002/0471264180.or050.01. ISBN 0471264180.
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