4081. Filixic Acids
Nomenclature
Filicin; filicic acid; Filixsure (German).Description and references
Natural filixic acid from male fern, Dryopteris filix-mas, is a mixture of six homologues, the 3 main components (BBB, PBB, PBP) of which are obtained by recrystallization from ethyl acetate. When raw filixic acid is purified by treatments with methanol but without recrystns from ethyl acetate, a product is obtained which seems to contain 3 additional homologues with an analogous composition but with acetyl groups in the side chain. Isoln: Luck, Ann. 54, 119 (1845); Boehm, ibid. 318, 253 (1901). Structure studies: Riedl, Ann. 585, 32 (1954); Chan, Hassal, Experientia 13, 349 (1957). Structure of the three main filixic acids: Penttil, Sundman, Acta Chem. Scand. 17, 191 (1963).
Properties
Natural filixic acid, pale-yellow plates from ethyl acetate, mp 184-185°. uv max: 228, 288 nm (ε 41000, 29000). Practically insol in water, methanol, acetone. Sol in chloroform, benzene, warm ethyl acetate, acetic acid; slightly sol in ether.Derivative
BBB.Nomenclature
CAS number: 4482-83-1
2,2′-[[2,4,6-Trihydroxy-5-(1-oxobutyl)-1,3-phenylene]bis(methylene)]bis[3,5-dihydroxy-4,4-dimethyl-6-(1-oxobutyl)-2,5-cyclohexadien-1-one]. C36H44O12; mol wt 668.73.
C 64.66%, H 6.63%, O 28.71%.
Properties
Crystals from ethyl acetate, mp 172-174°.Derivative
PBB.Nomenclature
CAS number: 49582-09-4
C35H42O12; mol wt 654.70.
C 64.21%, H 6.47%, O 29.33%.
Properties
Crystals from ethyl acetate, mp 184-186°.Derivative
PBP.Nomenclature
CAS number: 51005-85-7
C34H40O12; mol wt 640.67.
C 63.74%, H 6.29%, O 29.97%.