5262. Javanicin

Nomenclature

CAS number: 476-45-9
5,8-Dihydroxy-6-methoxy-2-methyl-3-(2-oxopropyl)-1,4-naphthalenedione; 3-acetonyl-5,8-dihydroxy-6-methoxy-2-methyl-1,4-naphthoquinone.
C15H14O6; mol wt 290.27.
C 62.07%, H 4.86%, O 33.07%.

Description and references

Antibiotic substance produced by Fusarium javanicum: Arnstein, Cook, J. Chem. Soc. 1947, 1021. Prepd by reduction of fusarubin: Ruelius, Gauhe, Ann. 569, 38 (1950). Structure: Birch, Donovan, Chem. Ind. (London) 1954, 1047; Whalley, ibid. 1958, 131; Hardegger et al., Helv. Chim. Acta 47, 2027 (1964).

Chemical structure

Properties

Red crystals with a coppery luster from ethanol, decomp 207.5-208°. Absorption max (alc): 303, 305 nm (log ε 3.97, 3.90); in chloroform: 307, 510 nm (log ε 3.99, 3.86).

Derivative

Diacetyljavanicin.
C19H18O8; mol wt 374.34.
C 60.96%, H 4.85%, O 34.19%.

Properties

Needles from dil acetone, dec 207-208°. Absorption max (alc): 221, 290, 426 nm (log ε 4.57, 4.17, 3.79).