Sterigmatocystin

Sterigmatocystin

Names
Preferred IUPAC name (3aR,12cS)-8-Hydroxy-6-methoxy-3a,12c-dihydro-7H-furo[3′,2′:4,5]furo[2,3-c]xanthen-7-one
Other names Sterigmatocystin
Identifiers
CAS Number	10048-13-2 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18227 Y
ChEMBL	ChEMBL524291 Y
ChemSpider	4447522 Y
ECHA InfoCard	100.030.131
EC Number	233-158-6
KEGG	C00961 Y
PubChem CID	5280389
UNII	5F95211S5Z Y
CompTox Dashboard (EPA)	DTXSID2021280
InChI InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1 N Key: UTSVPXMQSFGQTM-DCXZOGHSSA-N N
SMILES COC1=C2C(=C3[C@@H]4C=CO[C@@H]4OC3=C1)OC5=C(C2=O)C(=CC=C5)O
Properties
Chemical formula	C18H12O6
Molar mass	324.28 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Sterigmatocystin is a polyketide mycotoxin produced by certain species of Aspergillus. The toxin is naturally found in some cheeses.

Sterigmatocystin is a toxic metabolite structurally closely related to the aflatoxins as it is the penultimate precursor of aflatoxins B1 and G1.^[1] It contains a xanthone nucleus attached to a bifuran structure. Sterigmatocystin is mainly produced by the fungi Aspergillus nidulans and A. versicolor.

It has been reported in mouldy grain, green coffee beans and cheese although information on its occurrence in foods is limited. It appears to occur much less frequently than the aflatoxins, although analytical methods for its determination have not been as sensitive, and so it is possible that small concentrations in food commodities may not always have been detected. Although it is a potent liver carcinogen similar to aflatoxin B1, current knowledge suggests that it is nowhere near as widespread in its occurrence. If this is the true situation it would be justified to consider sterigmatocystin as no more than a risk to consumers in special or unusual circumstances. A number of closely related compounds such as o-methyl sterigmatocystin are known, and some may also occur naturally.