Structural Formula Vector Image
Title: Juglone
CAS Registry Number: 481-39-0
CAS Name: 5-Hydroxy-1,4-naphthalenedione
Additional Names: 5-hydroxy-1,4-naphthoquinone; 8-hydroxy-1,4-naphthoquinone; C.I. 75500; C.I. Natural Brown 7; nucin; regianin
Molecular Formula: C10H6O3
Molecular Weight: 174.15
Percent Composition: C 68.97%, H 3.47%, O 27.56%
Literature References: Coloring matter occurring in various Juglandaceae spp: Brissemoret, Combes, Compt. Rend. 141, 838 (1905). Isoln from walnut shells: Combes, Bull. Soc. Chim. 1(4), 800 (1907). Isoln and description of sedative properties in fish, mammals: B. A. Westfall et al., Science 134, 1617 (1961). Isoln from pecans and identification as inhibitory agent of mycelial growth of Fusicladium effusum: P. A. Hedin et al., J. Agric. Food Chem. 28, 340 (1980). Synthesis: Bernthsen, Semper, Ber. 20, 938 (1887); Willstätter, Wheeler, Ber. 47, 2798 (1914); Teuber, Götz, Ber. 87, 1236 (1954); C. Grundmann, Synthesis 1977, 644. Tumor-promoting activity study: B. L. Van Duuren et al., J. Med. Chem. 21, 26 (1978). Use as pH indicator: S. S. Sawhney, B. M. L. Bhatia, J. Indian Chem. Soc. 57, 438 (1980).
Properties: Yellow needles from benzene + petr ether, mp 155°. Sublimes. Absorption max (methanol): 420 nm (log e 3.56). Volatile with steam. Slightly sol in hot water; freely sol in chloroform, benzene; sol in alcohol, ether; sol in aq solns of alkalies giving a purplish-red soln.
Melting point: mp 155°
Absorption maximum: Absorption max (methanol): 420 nm (log e 3.56)

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