8408. Scopoletin

Nomenclature

CAS number: 92-61-5
7-Hydroxy-6-methoxy-2H-1-benzopyran-2-one; 7-hydroxy-6-methoxycoumarin; 6-methoxyumbelliferone; β-methylesculetin; chrysatropic acid; gelseminic acid.
C10H8O4; mol wt 192.17.
C 62.50%, H 4.20%, O 33.30%.

Description and references

The aglucone of scopolin. Occurs in root of Scopolia japonica Maxim., Scopolia carniolica Jacq., Atropa belladonna L., Solanaceae, Convolvulus scammonia L., Convolvulaceae. Isoln: Eykman, Ber. 17 III, 442 (1884). Synthesis: Crosby, J. Org. Chem. 26, 1215 (1961); Desai, Desai, J. Indian Chem. Soc. 40, 456 (1963).

Chemical structure

Properties

Needles or prisms from chloroform or acetic acid, mp 204°. uv max: 230, 254, 260, 298, 346 nm (log ε 4.11, 3.68, 3.63, 3.68, 4.07), Ballantyne et al., Tetrahedron 27, 871 (1971). Slightly sol in water or cold alcohol; sol in hot alcohol or hot glacial acetic acid; moderately sol in chloroform. Practically insol in benzene. Its alcoholic soln has a blue fluorescence. Reduces Fehling's soln.