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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:
Molecular Weight:
324.28
Beilstein:
53259
EC Number:
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

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

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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General description

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

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.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

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

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Certificates of Analysis (COA)

Lot/Batch Number

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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)
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)
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
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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