Perilla ketone explained

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 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

Notes and References

  1. Yeigai. Sebe. Supplemental experiments on perilla ketone . Nippon Kagaku Kaishi. 64. 8. 1130–6. 1943. 10.1246/nikkashi1921.64.1130. ja. free.
  2. http://www.hort.purdue.edu/newcrop/proceedings1993/V2-322.html Perilla: Botany, Uses and Genetic Resources
  3. Teruo. Matsuura. Natural furan derivatives. I. The synthesis of perilla ketone. Bulletin of the Chemical Society of Japan. 30. 430–1. 1957. 10.1246/bcsj.30.430. free.
  4. Vittorio. Farina. The Stille reaction. Organic Reactions. 50. 1–652. 1997. Krishnamurthy. Venkat . Scott . William J.. 10.1002/0471264180.or050.01. 0471264180.