STERIGMATOCYSTIN

STERIGMATOCYSTIN Basic information
Product Name:STERIGMATOCYSTIN
Synonyms:SterigMatocystin froM Aspergillus Versicolor;NSC 201423 NSC 204985 Sterigmatocystin;(3aR,12cS)-3a,12c-Dihydro-8-hydroxy-6-Methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one;NSC 201423;NSC 204985;(3aR,12cS)-8-hydroxy-6-methoxy-3aH-furo[3',2':4,5]furo[2,3-c]xanthen-7(12cH)-one;STERIGMATOCYSTIN;STERIGMATOCYSTIN, ASPERGILLUS VERSICOLOR
CAS:10048-13-2
MF:C18H12O6
MW:324.28
EINECS:233-158-6
Product Categories:
Mol File:10048-13-2.mol
STERIGMATOCYSTIN Structure
STERIGMATOCYSTIN Chemical Properties
Melting point 249-251℃
Boiling point 382.63°C (rough estimate)
density 1.2842 (rough estimate)
refractive index 1.4800 (estimate)
Fp 6℃
storage temp. 2-8°C
solubility Acetone: 5 mg/ml
pka6.92±0.20(Predicted)
form powder
color yellow
BRN 53259
LogP3.169 (est)
CAS DataBase Reference10048-13-2
IARC2B (Vol. 10, Sup 7) 1987
EPA Substance Registry SystemSterigmatocystin (10048-13-2)
Safety Information
Hazard Codes T,Xn,F
Risk Statements 25-40-36-20/21/22-11
Safety Statements 36/37-45-16
RIDADR UN 3462 6.1/PG 3
WGK Germany 3
RTECS LV1750000
10
HazardClass 6.1(b)
PackingGroup III
HS Code 29329990
Hazardous Substances Data10048-13-2(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
STERIGMATOCYSTIN Usage And Synthesis
DescriptionSterigmatocystin is a mycotoxin that has been found in Aspergillus. It is lethal to rats (LD50 = 60 mg/kg) and chick embryos (LD50s = 5-7 μg/embryo). Sterigmatocystin (100 and 1,000 ppb in drinking water) induces gastritis, as well as intestinal polyp formation and metaplasia in aged Mongolian gerbils. It induces formation of lung and liver adenomas and malignant lymphomas in newborn mice.
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.
Biochem/physiol ActionsInitiates lung and liver tumors under experimental conditions.
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.]
STERIGMATOCYSTIN Preparation Products And Raw materials
Preparation ProductsAFLATOXIN B1
1-(2-METHOXY-5-METHYLPHENYL)ETHANONE Phloroglucinol 2,2'-METHYLENEDIPHENOL 2,4'-DIHYDROXYDIPHENYLMETHANE NSC46644 5,6-dimethoxysterigmatocystin 2-HYDROXY-3-METHYLBENZALDEHYDE 1-ETHYL-3-ISO-PROPYLBENZENE 2-ETHYL-5-METHOXYPHENOL 2,4-Dihydroxy-3-methylbenzaldehyde 5-METHOXY-STERIGMATOCYSTIN 3-Methylbenzophenone CHEMBRDG-BB 6474172 4-Methoxybenzophenone O-ALLYLANISOLE 2',4',6'-TRIMETHOXYACETOPHENONE 2,6-DIETHYLPHENOL M-CYMENE

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