7538. Plumbagin

Nomenclature

CAS number: 481-42-5
5-Hydroxy-2-methyl-1,4-naphthalenedione; 5-hydroxy-2-methyl-1,4-naphthoquinone.
C11H8O3; mol wt 188.18.
C 70.21%, H 4.29%, O 25.51%.

Description and references

Found in the roots of Plumbago europaea L., P. zeylanica, P. rosea L., Plumbaginaceae. Isoln: Dulong d'Astafort, J. Pharm. Chim. 14, 441 (1828); Wefers-Bettink, Rec. Trav. Chim. 8, 319 (1889); Ray, Dutt, J. Indian Chem. Soc. 5, 419 (1928). Structure and synthesis: Fieser, Dunn, J. Am. Chem. Soc. 58, 572 (1936). Biosynthesis: Durand, Zenk, Tetrahedron Lett. 1971, 3009. Chemotherapeutic properties: Vichkanova et al., C.A. 78, 66906s (1973). Efficient syntheses: A. Ichihara et al., Agric. Biol. Chem. 44, 211 (1980); G. Wurm et al., Arch. Pharm. 314, 861, 1055 (1981); H. M"ohrle, H. Foltmann, ibid. 321, 259 (1988). Toxicity data: M. Debray et al., Plant Med. Phytother. 7, 77 (1973), C.A. 79, 14255e (1973).

Chemical structure

Properties

Yellow needles from dil alcohol, mp 78-79°. Sublimes. Volatile with steam. Slightly sol in hot water; sol in alc, acetone, chloroform, benzene, acetic acid. LD50 i.p. in mice: ≈0.015 g/kg (Debray).