Sterigmatocystin
| Code | Size | Price |
|---|
| BVT-0171-M001 | 1 mg | £65.00 |
Quantity:
| BVT-0171-M005 | 5 mg | £170.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4°C
Documents
Further Information
Alternate Names/Synonyms:
NSC 201423; NSC 204985
Appearance:
Pale yellow powder.
CAS:
10048-13-2
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS06,GHS08
Handling Advice:
Protect from light.
Hazards:
H301, H351
InChi:
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/t8-,18+/m0/s1
InChiKey:
UTSVPXMQSFGQTM-DCXZOGHSSA-N
Long Description:
Chemical. CAS: 10048-13-2. Formula: C18H12O6. MW: 324.3. Isolated from Aspergillus sp. (strain WDMH51). Intermediate of the biosynthetic pathway to aflatoxin B1. Mycotoxin. DNA synthesis inhibitor. Anticancer compound. Cytotoxic, carcinogenic and mutagenic. Acyl-CoA:cholesterol acyltransferase 2 (ACAT2) inhibitor. Shown to induce apoptosis in human peripheral lymphocytes and necrosis in rat liver. Induces sister chromatid exchanges in murine bone marrow cells.
MDL:
MFCD32182631
Molecular Formula:
C18H12O6
Molecular Weight:
324.3
Package Type:
Plastic Vial
PG:
III
Precautions:
P201, P281, P301, P310, P405
Product Description:
Intermediate of the biosynthetic pathway to aflatoxin B1. Mycotoxin. DNA synthesis inhibitor. Anticancer compound. Cytotoxic, carcinogenic and mutagenic. Acyl-CoA:cholesterol acyltransferase 2 (ACAT2) inhibitor. Shown to induce apoptosis in human peripheral lymphocytes and necrosis in rat liver. Induces sister chromatid exchanges in murine bone marrow cells.
Purity:
>98% (HPLC; NMR)
Signal word:
Danger
SMILES:
[H][C@]12OC=C[C@@]1([H])C1=C3OC4=C(C(O)=CC=C4)C(=O)C3=C(OC)C=C1O2
Solubility Chemicals:
Soluble in DMSO, ethanol, methanol, pyridine or acetone.
Source / Host:
Isolated from Aspergillus sp. (strain WDMH51).
Transportation:
Excepted Quantity
UN Nummer:
UN 3462
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 1 year after receipt when stored at -20°C. After reconstitution protect from light at -20°C.
References
Sterigmatocystin, a metabolite of Aspergillus versicolor: J. E. Davies, et al.; J. Chem. Soc. 1960, 2169 (1960) | Massive and single cell necrosis in the rat liver induced by aflatoxin B1 and sterigmatocystin: K. Terao; Acta Pathol. Jpn. 23, 647 (1973) | Fermentation, isolation, and antitumor activity of sterigmatocystins: W.T. Bradner, et al.; Antimicrob. Agents Chemother. 8, 159 (1975) | Biosynthesis of aflatoxins. Incorporation of acetate into sterigmatocystin in Aspergillus versicolor: T. J. Simpson and D. J. Stenzel; JCS Chem. Commun. 1982, 890 (1982) | Induction of sister-chromatid exchanges in vivo in mice by the mycotoxins sterigmatocystin and griseofulvin: P.T. Curry, et al.; Mutat. Res. 137, 111 (1984) | Inhibitory effect of sterigmatocystin and 5,6-dimethoxysterigmatocystin on ATP synthesis in mitochondria: K. Kawai, et al.; Appl. Environ. Microbiol. 48, 1001 (1984) | Effects of sterigmatocystin, deoxynivalenol and aflatoxin G1 on apoptosis of human peripheral blood lymphocytes in vitro: X.M. Sun, et al.; Biomed. Environ. Sci. 15, 145 (2002) | Cytotoxicity of occupationally and environmentally relevant mycotoxins: J. Bunger, et al.; Toxicology 202, 199 (2004) | Selective inhibition of Acyl-CoA: cholesterol acyltransferase 2 isozyme by flavasperone and Sterigmatocystin from Aspergillus species: K. Sakai, et al.; J. Antibiot. 61, 568 (2008) | Bioactive metabolites from the sponge-derived fungus Aspergillus versicolor: Y. M. Lee, et al.; Arch. Pharm. Res. 33, 231 (2010) | Long-term administration of the fungus toxin, Sterigmatocystin, induces intestinal metaplasia and increases the proliferative activity of PCNA, p53, and MDM2 in the gastric mucosa of aged Mongolian gerbils: M. Kusunoki, et al.; Environ Health Prev. Med. 16, 224 (2011) | Effects of Sterigmatocystin on TNF-alpha, IL-6 and IL-12 expression in murine peripheral blood mononuclear cells and peritoneal macrophages in vivo: Y. Zhang, et al.; Mol. Med. Rep. 5, 1318 (2012) | Emerging Mycotoxins: Beyond Traditionally Determined Food Contaminants: C. Gruber-Dorninger, et al.; J. Agr. Food Chem. 65, 7052 (2017) | Cytotoxic effects induced by patulin, sterigmatocystin and beauvericin on CHO-K1 cells: N. Zouaoui, et al.; Food Chem. Toxicol. 89, 92 (2016) | A highly specific competitive direct enzyme immunoassay for sterigmatocystin as a tool for rapid immunochemotaxonomic differentiation of mycotoxigenic Aspergillus species: S. Wegner, et al.; Lett. Appl. Microbiol. 64, 124 (2017)
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