Title: Indican (Plant Indican)
CAS Registry Number: 487-60-5
CAS Name: 1H-Indol-3-yl-b-D-glucopyranoside
Additional Names: 3-(b-glucosido)indole; indoxyl-b-D-glucoside
Molecular Formula: C14H17NO6
Molecular Weight: 295.29
Percent Composition: C 56.94%, H 5.80%, N 4.74%, O 32.51%
Literature References: Isolated from Indigofera spp., Leguminosae and from Polygonum tinctorium Ait., Polygonaceae. Extraction procedure for the glucoside: Hoogewerff, Meulen, Rec. Trav. Chim. 19, 166 (1900); Perkin, Bloxam, J. Chem. Soc. 91, 1715 (1907); Perkin, Thomas, ibid. 95, 793 (1909). About 3% indican is found in 4-day old air-dried leaves of Indigofera tinctoria. Synthesis: Robertson, J. Chem. Soc. 1927, 1937; Robertson, Waters, ibid. 1933, 30; Freudenberg et al., Ber. 85, 641 (1952).
Derivative Type: Trihydrate
Properties: Orthorhombic spear-shaped needles, mp 57-58°. [a]19546 -66°. After heating in vacuo (oil pump) over H2SO4 for 48 hrs the hemihydrate is obtained, mp 101°. Robertson obtained the anhydrous compound by heating in the steam oven for 3 hrs, at 110° for 1 hr, and at 160° for 5 minutes. Perkin and Bloxam obtained anhydr indican by treating the trihydrate with boiling alcohol and boiling benzene. Anhydr indican decomposes at 178-180°. [a]D15 -66° (c = 2); [a]19546 -78° (c = 0.6). Sol in water, methanol, alcohol, acetone; slightly sol in ether, benzene, chloroform, ethyl acetate, carbon disulfide. Anhydr indican is sparingly sol in anhydr alcohol.
Melting point: mp 57-58°; mp 101°
Optical Rotation: [a]19546 -66°; [a]D15 -66° (c = 2); [a]19546 -78° (c = 0.6)
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