All Photos(1)

S3255

Sigma-Aldrich

Sterigmatocystin

powder, ≥98% (TLC)

Synonym(s):
3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furol[3′,2′:4,5]furo[2,3-c]xanthen-7-one
Empirical Formula (Hill Notation):
C18H12O6
CAS Number:
Molecular Weight:
324.28
Beilstein:
53259
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥98% (TLC)

form

powder

color

yellow

storage temp.

−20°C

SMILES string

COc1cc2OC3OC=CC3c2c4Oc5cccc(O)c5C(=O)c14

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

InChI key

UTSVPXMQSFGQTM-UHFFFAOYSA-N

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Packaging

1, 5 mg in serum bottle

Biochem/physiol Actions

Initiates lung and liver tumors under experimental conditions.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Daniela Jakšić et al.
Archives of toxicology, 86(10), 1583-1591 (2012-06-01)
Aspergillus versicolor and A. flavus are primary colonizers in damp dwellings, and they produce sterigmatocystin (ST) and aflatoxin B1 (AFB(1)), respectively. These hepatotoxic and carcinogenic mycotoxins and their precursors and derivates possess a furofuran ring, which has proven responsible for...
Jason C Slot et al.
Current biology : CB, 21(2), 134-139 (2011-01-05)
Genes involved in intermediary and secondary metabolism in fungi are frequently physically linked or clustered. For example, in Aspergillus nidulans the entire pathway for the production of sterigmatocystin (ST), a highly toxic secondary metabolite and a precursor to the aflatoxins...
Hans-Wilhelm Nützmann et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(34), 14282-14287 (2011-08-10)
Sequence analyses of fungal genomes have revealed that the potential of fungi to produce secondary metabolites is greatly underestimated. In fact, most gene clusters coding for the biosynthesis of antibiotics, toxins, or pigments are silent under standard laboratory conditions. Hence...
Hans-Wilhelm Nützmann et al.
Applied and environmental microbiology, 79(19), 6102-6109 (2013-07-31)
Chromatin remodelling events play an important role in the secondary metabolism of filamentous fungi. Previously, we showed that a bacterium, Streptomyces rapamycinicus, is able to reprogram the histone-modifying Spt-Ada-Gcn5-acetyltransferase/ADA (SAGA/ADA) complex of the model fungus Aspergillus nidulans. Consequently, the histone...
Juan Wang et al.
Toxicology letters, 217(3), 226-234 (2013-01-09)
Sterigmatocystin (ST), a common environmental contaminant found across the world, is generally recognized as a potential carcinogen, mutagen and teratogen. Our previous epidemiological studies suggested that ST exposure might be a risk factor for esophageal cancer. However, the direct effects...

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