Cycasin
Title: Cycasin
CAS Registry Number: 14901-08-7
CAS Name: (Methyl-ONN-azoxy)methyl b-D-glucopyranoside
Additional Names: methylazoxymethanol b-D-glucoside; b-D-glucosyloxyazoxymethane
Molecular Formula: C8H16N2O7
Molecular Weight: 252.22
Percent Composition: C 38.10%, H 6.39%, N 11.11%, O 44.40%
Literature References: Toxic substance from seeds of Cycas revoluta Thumb. and C. circinalis L., Cycadaceae from Guam: Nishida et al., Bull. Agric. Chem. Soc. Jpn. 19, 77 (1955), C.A. 50, 13756g (1956); Riggs, Chem. Ind. (London) 1956, 926; Matsumoto, Strong, Arch. Biochem. Biophys. 101, 299 (1963). Biological effects, metabolism and mechanism of action of cycasin and its aglycone, methylazoxymethanol: Spatz, Ann. N.Y. Acad. Sci. 163, 848 (1969). Structure: Korsch, Riggs, Tetrahedron Lett. 1964, 523. Toxicology: Laqueur, Spatz, Cancer Res. 28, 2262 (1968). Carcinogenicity and neurotoxicity studies: I. Hirono, Fed. Proc. 31, 1493 (1972). Review of carcinogenicity studies: IARC Monographs 10, 121-138 (1976).
Properties: Needles from water + acetone + ether, dec 154°. [a]D18 -44° (c = 0.62). uv max (0.4M H2SO4): 217 nm. LD50 in rats, mice, hamsters, rabbits, guinea pigs (mg/kg): 562, 500, <250, ~30, <20 orally (Hirono).
Optical Rotation: [a]D18 -44° (c = 0.62)
Absorption maximum: uv max (0.4M H2SO4): 217 nm
Toxicity data: LD50 in rats, mice, hamsters, rabbits, guinea pigs (mg/kg): 562, 500, <250, ~30, <20 orally (Hirono)
 
Derivative Type: Tetraacetate
Molecular Formula: C16H24N2O11
Molecular Weight: 420.37
Percent Composition: C 45.71%, H 5.75%, N 6.66%, O 41.87%
Properties: Plates from acetone + petr ether, mp 137°. [a]D18 -27° (c = 0.98 in CHCl3).
Melting point: mp 137°
Optical Rotation: [a]D18 -27° (c = 0.98 in CHCl3)
 
CAUTION: Cycasin has been listed as reasonably anticipated to be a carcinogen: Fourth Annual Report on Carcinogens (NTP 85-002, 1985) p 64; delisted because no U.S. residents exposed: Fifth Annual Report on Carcinogens (NTP 89-239, 1989) p 340.

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