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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

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About This Item

Empirical Formula (Hill Notation):
C18H12O6
CAS Number:
10048-13-2
Molecular Weight:
324.28
Beilstein:
53259
EC Number:
233-158-6
MDL number:
MFCD00005084
UNSPSC Code:
85151701
PubChem Substance ID:
24899549
NACRES:
NA.25

Quality Level

200

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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Biochem/physiol Actions

Initiates lung and liver tumors under experimental conditions.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H351

Precautionary Statements

P201 - P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
Xin Xing et al.
Molecular nutrition & food research, 55(5), 749-760 (2011-02-03)
Sterigmatocystin (ST), a mycotoxin commonly found in foodstuff and feedstuff, has been shown to be a carcinogenic mycotoxin in animal models. Many studies showed that the high level of ST contamination in grains might be related to the high incidence
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.
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
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