4315. Fusarubin

Nomenclature

CAS number: 1702-77-8
3,4-Dihydro-3,6,9-trihydroxy-7-methoxy-3-methyl-1H-naphtho[2,3-c]pyran-5,10-dione; 5,8-dihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-1,4-naphthalenedione; 3-acetonyl-5,8-dihydroxy-2-(hydroxymethyl)-6-methoxy-1,4-naphthoquinone; oxyjavanicin.
C15H14O7; mol wt 306.27.
C 58.82%, H 4.61%, O 36.57%.

Description and references

Isoln from Fusarium solani: Ruelius, Gauhe, Ann. 569, 38 (1950). Structure: Hardegger et al., Helv. Chim. Acta 47, 2027 (1964). Efficient total synthesis: Y. Tanoue et al., Bull. Chem. Soc. Jpn. 60, 2927 (1987).

Chemical structure

Properties

Red prisms from benzene, dec 218°. Absorption max (ether): 535, 499 nm. Sol in glacial acetic acid, tetrahydrofuran, acetone, dioxane, pyridine; slightly sol in cold chloroform, cold alcohol, ether. Practically insol in carbon disulfide, cyclohexane, cold benzene. Dissolves in dil NaOH with a violet color. Practically insol in bicarbonate soln.