Glucofrangulin

Title: Glucofrangulin
CAS Registry Number: 52731-38-1
Trademarks: Erbalax-N (Erba); Irgalax (Novartis)
Molecular Formula: C27H30O14
Molecular Weight: 578.52
Percent Composition: C 56.05%, H 5.23%, O 38.72%
Literature References: Anthraquinone glycoside from bark of Rhamnus frangula L., Rhamnaceae (alder buckthorn): Casparis, Maeder, Bull. Soc. Chim. Biol. 9, 324 (1927); Cucu, Jarpo, Pharmazie 14, 316 (1959); Knap et al., CS 110024 (1964), C.A. 61, 4159e (1964). Consists of two isomers, glucofrangulin A and glucofrangulin B, which differ by the linkage to the sugar moiety at the 3 position of the aglycone. Structure: Schindler, Helv. Chim. Acta 29, 411 (1946); Hörhammer et al., Naturwissenschaften 51, 310 (1964); Longo et al., Arch. Pharm. 297, 248 (1964); Wagner, Hörhammer, Naturwissenschaften 53, 585 (1966). Proof of structure of glucofrangulin A and partial synthesis: eidem, Z. Naturforsch. 24B, 1408 (1969).
Derivative Type: Glucofrangulin A
CAS Registry Number: 21133-53-9
Additional Names: 3-[(6-Deoxy-a-L-mannopyranosyl)oxy]-1-(b-D-glucopyranosyloxy)-8-hydroxy-6-methyl-9,10-anthracenedione
Derivative Type: Glucofrangulin A octaacetate
Molecular Formula: C43H46O22
Molecular Weight: 914.81
Percent Composition: C 56.46%, H 5.07%, O 38.48%
Properties: Needles from methanol, mp 228-230°. [a]D20 -124° (c = 1.16 in acetone). uv max: 212, 264, 360 nm (log e 4.57, 4.56, 4.26).
Melting point: mp 228-230°
Optical Rotation: [a]D20 -124° (c = 1.16 in acetone)
Absorption maximum: uv max: 212, 264, 360 nm (log e 4.57, 4.56, 4.26)
Therap-Cat: Cathartic.
Keywords: Laxative/Cathartic.
Glucoheptonic Acid Gluconic Acid Gluconolactone Glucosamine Glucose Oxidase