Title: Herqueinone
CAS Registry Number: 26871-30-7
CAS Name: (7aS,9R)-8,9-Dihydro-4,6,7a-trihydroxy-5-methoxy-1,8,8,9-tetramethyl-3H-phenaleno[1,2-b]furan-3,7(7aH)-dione
Molecular Formula: C20H20O7
Molecular Weight: 372.37
Percent Composition: C 64.51%, H 5.41%, O 30.08%
Literature References: Red fungal pigment isolated from Penicillium herquei: Stodola et al., Nature 167, 773 (1951); Galarraga et al., Biochem. J. 61, 456 (1955); Harman et al., J. Org. Chem. 20, 1260 (1955). Structure: Cason et al., Tetrahedron 18, 839 (1962); Paul, Sim, Proc. Chem. Soc. London 1962, 352; Cason et al., J. Org. Chem. 35, 179 (1970); J. S. Brooks, G. A. Morrison, Tetrahedron Lett. 1970, 963; eidem, J. Chem. Soc. Perkin Trans. 1 1972, 421; 1974, 2114. Crystal structure and abs config: A. Quick et al., Chem. Commun. 1980, 1051. 13C-NMR study: T. Suga et al., Chem. Lett. 1981 1063.
Properties: Red needles from alc, dec 226°. Sublimes in high vacuum at 175-190°. Absorption max (ethanol): 220, 250, 314, 416 nm (log e 4.29, 4.09, 4.47, 3.66). Sol in acetone, DMF, 2N NaOH, concd HCl, cold concd H2SO4; fairly sol in methanol, ethanol, ether, ethyl acetate, chloroform; slightly sol in benzene, carbon disulfide. Practically insol in petr ether, carbon tetrachloride, water, aq Na2CO3.
Absorption maximum: Absorption max (ethanol): 220, 250, 314, 416 nm (log e 4.29, 4.09, 4.47, 3.66) |