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Merck
CN

S3255

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
UNSPSC Code:
85151701
NACRES:
NA.25
PubChem Substance ID:
24899549
EC Number:
233-158-6
Beilstein/REAXYS Number:
53259
MDL number:
MFCD00005084

Key Documents

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Product Name

Sterigmatocystin, powder, ≥98% (TLC)

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

SMILES string

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

assay

≥98% (TLC)

form

powder

color

yellow

storage temp.

−20°C

Quality Level

200

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Biochem/physiol Actions

Initiates lung and liver tumors under experimental conditions.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H301,H351

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

高风险级别生物产品--毒素类产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000452403
0000452403
0000425139
0000425139
0000410633

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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
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
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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