Cycasin

Cycasin

Names
Systematic IUPAC name [(E)-Methyl-ONN-azoxy]methyl β-D-glucopyranoside
Other names β-D-Glucosyloxyazoxymethane; Methylazoxymethanol β-D-glucoside; Cycas revoluta glucoside
Identifiers
CAS Number	14901-08-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:CHEBI:17074
ChemSpider	4573631
KEGG	C01418
MeSH	D003492
PubChem CID	5459896
InChI InChI=1S/C8H16N2O7/c1-10(15)9-3-16-8-7(14)6(13)5(12)4(2-11)17-8/h4-8,11-14H,2-3H2,1H3/b10-9+/t4-,5-,6+,7-,8-/m1/s1 Key: YHLRMABUJXBLCK-IRCVIWNGSA-N InChI=1/C8H16N2O7/c1-10(15)9-3-16-8-7(14)6(13)5(12)4(2-11)17-8/h4-8,11-14H,2-3H2,1H3/b10-9+/t4-,5-,6+,7-,8-/m1/s1 Key: YHLRMABUJXBLCK-IRCVIWNGBN
SMILES [O-]/[N+](=N/CO[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)C
Properties
Chemical formula	C8H16N2O7
Molar mass	252.22 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cycasin is a phytotoxin found in cycads such as Cycas revoluta and Zamia pumila. Both plants are used to produce sago. The butterfly Eumaeus atala, whose larvae feed on Z. pumila, also contains the compound. The seeds of C. revoluta contain the highest level of the toxin.

It induces hepatotoxicity and Zamia staggers, a fatal nervous disease affecting cattle where they browse on the leaves or fruit of cycads.

The enzyme methyl-ONN-azoxymethanol beta-D-glucosyltransferase uses the two substrates UDP-glucose and methyl-ONN-azoxymethanol to produce UDP and cycasin.