Title: Atractyloside
CAS Registry Number: 17754-44-8
CAS Name: (2b,4a,15a)-15-Hydroxy-2-[[2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-b-D-glucopyranosyl]oxy]-19-norkaur-16-en-18-oic acid dipotassium salt
Additional Names: potassium atractylate; atractylin (C30 glucoside)
Molecular Formula: C30H44K2O16S2
Molecular Weight: 802.99
Percent Composition: C 44.87%, H 5.52%, K 9.74%, O 31.88%, S 7.99%
Literature References: Toxic principle isolated from the thistle Atractylis gummifera L., Compositae: M. Lefranc, Compt. Rend. 67, 954 (1868). Structure and stereochemistry of the aglycone, atractyligenin: F. Piozzi et al., Tetrahedron Suppl. 8 II, 515 (1966); total synthesis of (±)-form: A. K. Singh et al., J. Am. Chem. Soc. 109, 6187 (1987). Structure and stereochemistry of atractyloside: eidem, Gazz. Chim. Ital. 97, 935 (1967). Toxicity studies: G. Cascio et al., Boll. Soc. Ital. Biol. Sper. 44, 253 (1968). Review: Atractyloside: Chemistry, Biochemistry, and Toxicology, R. Santi, S. Luciani, Eds. (Piccin Medical Books, Padova, Italy, 1978) 136 pp.
Properties: Crystals, dec 174°. [a]D20 -53° (water). Highly toxic! Has strychnine-like action; produces convulsion of a hypoglycemic nature: R. Santi, G. Cascio, C.A. 50, 7320i (1956); R. Santi, C.A. 52, 15733c (1958). LD50 i.m. in rats: 431 mg/kg (Cascio).
Optical Rotation: [a]D20 -53° (water)
Toxicity data: LD50 i.m. in rats: 431 mg/kg (Cascio) |