7166. Perilla Ketone

Nomenclature

CAS number: 553-84-4
1-(3-Furanyl)-4-methyl-1-pentanone; 1-(3-furyl)-4-methyl-1-pentanone; β-furyl isoamyl ketone.
C10H14O2; mol wt 166.22.
C 72.26%, H 8.49%, O 19.25%.

Description and references

Potent pulmonary edematogenic agent. Isoln from the mint plant, Perilla frutescens Britton, Labiatae, and structure: R. Goto, J. Pharm. Soc. Jpn. 57, 77 (1937). Synthesis: T. Matsuura, Bull. Chem. Soc. Jpn. 30, 430 (1957); K. Kondo, M. Matsumoto, Tetrahedron Lett. 1976, 4363; T. Kitamura et al., Synth. Commun. 7, 521 (1977); K. Inomata et al., Chem. Lett. 1979, 709. Potent lung toxin implicated in emphysema of grazing cattle: B. J. Wilson et al., Science 197, 573 (1977).

Chemical structure

Properties

Colorless oil, bp 196°. nD20 1.4781; d1515 0.9920. uv max (ethanol): 207, 253 nm (ε 14100, 5800). Sensitive to oxygen; becomes reddish-orange on standing. LD50 in female, male mice, male rats (mg/kg): 2.5, 6, 10 i.p. (Wilson).