Neoquassin
Title: Neoquassin
CAS Registry Number: 76-77-7
CAS Name: 16-Hydroxy-2,12-dimethoxypicrasa-2,12-diene-1,11-dione
Additional Names: 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
Molecular Formula: C22H30O6
Molecular Weight: 390.47
Percent Composition: C 67.67%, H 7.74%, O 24.58%
Literature 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).
Properties: Very bitter polymorphous crystals. Stable form, thick prisms, mp 227.5-228.5°; unstable form, long narrow plates, mp 213°. [a]D20 +41.0° (c = 4.98 in chloroform). uv max ~255 nm (e ~11,650). Sol in cold acetone, chloroform, pyridine, acetic acid, in warm ethyl acetate, benzene, alcohol. Sparingly sol in ether, petr ether.
Melting point: mp 227.5-228.5°; mp 213°
Optical Rotation: [a]D20 +41.0° (c = 4.98 in chloroform)
Absorption maximum: uv max ~255 nm (e ~11,650)

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