Nomenclature
CAS number: 26871-30-7
(7a
S,9
R)-8,9-Dihydro-4,6,7a-trihydroxy-5-methoxy-1,8,8,9-tetramethyl-3
H-phenaleno[1,2-
b]furan-3,7(7a
H)-dione.
C
20H
20O
7; mol wt 372.37.
C 64.51%, H 5.41%, O 30.08%.
Description and 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 ε 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.