4090. Flavaspidic Acid

Nomenclature

CAS number: 114-42-1
3,5-Dihydroxy-4,4-dimethyl-2-(1-oxobutyl)-6-[[2,4,6-trihydroxy-3-methyl-5-(1-oxobutyl)phenyl]methyl]-2,5-cyclohexadien-1-one; 3′-[(5-butyryl-2,4-dihydroxy-3,3-dimethyl-6-oxo-1,4-cyclohexadien-1-yl)methyl]-5′-methylphlorobutyrophenone; polystichocitrin; Toxifren.
C24H30O8; mol wt 446.49.
C 64.56%, H 6.77%, O 28.67%.

Description and references

Isolated from the rhizomes of male fern: Boehm, Ann. 318, 253 (1901); 329, 310 (1903). Structure and synthesis: McGookin et al., J. Chem. Soc. 1953, 1828; Riedl, Ann. 585, 32 (1954); Aebi, Helv. Chim. Acta 39, 153 (1956). Crystal structure of α- and β-forms: Ermets, Penttil, Acta Chem. Scand. 24, 3335 (1970). Toxicity study: Airaksinen et al., Acta Pharmacol. Toxicol. 25, 33 (1967).

Chemical structure

Derivative

α-Form.

Properties

Orthorhombic crystals from methanol or ethanol, mp 92°; solidifies again at 110° and melts again at 156°. LD50 orally in mice: 690 mg/kg (Airaksinen).

Derivative

β-Form.

Properties

Monoclinic crystals from benzene, xylene or acetic acid, mp 156°.