6463. Neoquassin

Nomenclature

CAS number: 76-77-7
16-Hydroxy-2,12-dimethoxypicrasa-2,12-diene-1,11-dione; 3a,4,5,6a,7,7a,8,11a,11b,11c-decahydro-5-hydroxy-2,10-dimethoxy-3,8,11a,11c-tetramethylphenanthro[10,1-bc]pyran-1,11-dione.
C22H30O6; mol wt 390.47.
C 67.67%, H 7.74%, O 24.58%.

Description and references

Found together with the quassin in the mixture of bitter constituents of the wood of Quassia amara L., Simaroubaceae, known in commerce as Surinam quassia. Forms quassin on oxidation. Isoln: London et al., J. Chem. Soc. 1950, 3431. Structure: Valenta et al., Tetrahedron Lett. 1960(20), 25; Carman, Ward, ibid. 1961, 317; Valenta et al., Tetrahedron 15, 100 (1961).

Chemical structure

Properties

Very bitter polymorphous crystals. Stable form, thick prisms, mp 227.5-228.5°; unstable form, long narrow plates, mp 213°. [α]D20 +41.0° (c = 4.98 in chloroform). uv max ≈255 nm (ε ≈11,650). Sol in cold acetone, chloroform, pyridine, acetic acid, in warm ethyl acetate, benzene, alcohol. Sparingly sol in ether, petr ether.