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Merck
CN

32609

Sterigmatocystin

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.24
PubChem Substance ID:
329754270
EC Number:
233-158-6
Beilstein/REAXYS Number:
53259
MDL number:
MFCD00005084

Key Documents

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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

grade

analytical standard
reference material

manufacturer/tradename

Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

storage temp.

−20°C

Quality Level

200

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Sterigmatocystin may be used as an analytical reference standard for the determination of the analyte in:
  • Grain samples by high-performance liquid chromatography-electrospray positive ionization-tandem mass spectrometry (HPLC-ESI+-MS/MS).
  • Sweet pepper samples by LC-ESI+-MS/MS.

Biochem/physiol Actions

Initiates lung and liver tumors under experimental conditions.

General description

Sterigmatocystin is classified under the mycotoxin family of compounds that is usually produced by fungi of several species of Aspergillus.

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 P2 (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
BCCG5937
BCBZ9352
BCBT5402

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Multiresidue mycotoxin analysis in wheat, barley, oats, rye and maize grain by high-performance liquid chromatography-tandem mass spectrometry.
Martos P, et al.
World Mycotoxin Journal, 3(3), 205-223 (2010)
Development of a multi-mycotoxin liquid chromatography/tandem mass spectrometry method for sweet pepper analysis.
Monbaliu S, et al.
Rapid Communications in Mass Spectrometry, 23(1), 3-11 (2009)
Analytical method for the determination of sterigmatocystin in grains using high-performance liquid chromatography-tandem mass spectrometry with electrospray positive ionization.
Ver?ilovskis A, et al.
Journal of Chromatography A, 1157(1-2), 467-471 (2007)
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
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