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STERIGMATOCYSTIN

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STERIGMATOCYSTIN Basic information
STERIGMATOCYSTIN Chemical Properties
  • Melting point:249-251℃
  • Boiling point:382.63°C (rough estimate)
  • Density 1.2842 (rough estimate)
  • refractive index 1.4800 (estimate)
  • Flash point:6℃
  • storage temp. 2-8°C
  • form powder
  • pka6.92±0.20(Predicted)
  • color yellow
  • BRN 53259
  • CAS DataBase Reference10048-13-2
  • IARC2B (Vol. 10, Sup 7) 1987
  • EPA Substance Registry SystemSterigmatocystin (10048-13-2)
Safety Information
MSDS
STERIGMATOCYSTIN Usage And Synthesis
  • Chemical Propertiesyellow needles or powder
  • UsesSterigmatocystin is a carcinogenic mycotoxin that is struturally related to Aflatoxin. Sterigmatocystin has been shown to inhibit RNA synthesis in rat liver nuclei.
  • UsesSterigmatocystin is a xanthone produced by several species of Aspergillus, isolated by a number of research groups in the 1950s as a mycotoxin associated with food and grain contamination. Sterigmatocystin is structurally related to the aflatoxins and, while it is considered to be mutagenic, teratogenic and carcinogenic, it is less widespread and potent than the aflatoxins. Sterigmatocystin, in the presence of microsomes, covalently binds to DNA. It uncouples oxidative phosphorylation but, unlike the aflatoxins, does not induce mitochondrial swelling or hinder Ca2+-induced swelling of mitochondria. Sterigmatocystin also inhibits acyl-CoA:cholesterol acyltransferase (ACAT) with selectivity for the ACAT2 isoenzyme.
  • DefinitionChEBI: An organic heteropentacyclic compound whose skeleton comprises a xanthene ring system ortho-fused to a dihydrofuranofuran moiety. The parent of the class of sterigmatocystins.
  • HazardPossible carcinogen; tumorigen; poison; mutagen; causes necrosis of the liver and kidney, and an inhibitory effect on orotic acid incorporation into nuclear RNA.
  • Safety ProfileConfirmed carcinogen with experimental carcinogenic and tumorigenic data. Poison by ingestion and intraperitoneal routes. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Purification MethodsIt crystallises from amyl acetate, Me2CO or EtOH and sublimes in vacuo. It has UV max at 208, 235, 249 and 329nm (log  4.28, 4.39, 4.44 and 4.12). [UV: Bullock et al. J Chem Soc 4179, 1962, UV, IR: Holker & Mulheirn J Chem Soc, Chem Commun 1576, 1576 1968, Birkinshaw & Hammady Biochem J 65 162 1957.] This mycotoxin induces bone marrow changes in mice [Curry et al. Mutation Res 137 111 1984]. [Beilstein 19/10 V 575.]
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