Filicinic Acid
Structural Formula Vector Image
Title: Filicinic Acid
CAS Registry Number: 2065-00-1
CAS Name: 3,5-Dihydroxy-4,4-dimethyl-2,5-cyclohexadien-1-one
Additional Names: 1,1-dimethylcyclohexane-2,4,6-trione; gem-dimethylphloroglucinol; filicinsäure (German)
Molecular Formula: C8H10O3
Molecular Weight: 154.16
Percent Composition: C 62.33%, H 6.54%, O 31.14%
Literature 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).
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.
Melting point: mp 214-215° (dec)
pKa: pK 5.8
Derivative Type: 3,5-Diacetylfilicinic acid
Molecular Formula: C12H14O5
Molecular Weight: 238.24
Percent Composition: 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.
Melting point: mp 65-66°
pKa: pK 5.0

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