4079. Filicinic Acid

Nomenclature

CAS number: 2065-00-1
3,5-Dihydroxy-4,4-dimethyl-2,5-cyclohexadien-1-one; 1,1-dimethylcyclohexane-2,4,6-trione; gem-dimethylphloroglucinol; filicinsure (German).
C8H10O3; mol wt 154.16.
C 62.33%, H 6.54%, O 31.14%.

Description and references

Isolated from male fern and by hydrolytic decompn of filixic acid or aspidin: Boehm, Ann. 302, 171 (1898); 329, 321 (1903). Synthesis: Robertson, Sandrock, J. Chem. Soc. 1933, 1617; Angus et al., Chem. Ind. (London) 1954, 546; Inagaki et al., J. Pharm. Soc. Jpn. 76, 1258 (1956); Hoefer, Riedl, Angew. Chem. 74, 501 (1962); eidem, Ann. 656, 127 (1962).

Chemical structure

Properties

Prisms from water or benzene, mp 214-215° (dec). pK 5.8. Practically insol in water, petr ether. Sol in 70 parts boiling water, 10 parts boiling alcohol; sparingly sol in ether, benzene, glacial acetic acid. Reduces Tollen's reagent.

Derivative

3,5-Diacetylfilicinic acid.
C12H14O5; mol wt 238.24.
C 60.50%, H 5.92%, O 33.58%.

Properties

Crystals from methanol, mp 65-66°. pK 5.0. Sol in cold methanol, benzene, ether; slightly sol in hot water.