Sterigmatocystin
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Category | Mycotoxins |
Catalog number | BBF-04644 |
CAS | 10048-13-2 |
Molecular Weight | 324.28 |
Molecular Formula | C18H12O6 |
Purity | >95% by HPLC |
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Description
Sterigmatocystin is a mycotoxin produced by several species of aspergillus. It is structurally related to the aflatoxins. It is mutagenic, teratogenic and carcinogenic and is less widespread and potent than Aflatoxin. It inhibits acyl-CoA. It is a cholesterol acyltransferase (ACAT) with selectivity for the ACAT2 isoenzyme.
Specification
Synonyms | (3aR,12cS)-3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one; (3aR-cis)-3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one; NSC 201423; NSC 204985; Sterigmatocystine |
Storage | Store at -20°C |
IUPAC Name | (3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one |
Canonical SMILES | COC1=C2C(=C3C4C=COC4OC3=C1)OC5=CC=CC(=C5C2=O)O |
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 |
InChI Key | UTSVPXMQSFGQTM-DCXZOGHSSA-N |
Source | Sterigmatocystin have usually been on mouldy, or poor quality materials such as wheat, maize, animal feed, hard cheese, pecan nuts and green coffee beans. |
Properties
Appearance | Pale Yellow to Light Yellow Solid |
Boiling Point | 569.7°C at 760 mmHg |
Melting Point | >230°C (dec.) |
Density | 1.51 g/cm3 |
Solubility | Soluble in DMF, DMSO; Moderately soluble in Methanol, Ethanol, Chloroform; Poorly soluble in Water |
Toxicity
Carcinogenicity | 2B, possibly carcinogenic to humans. |
Mechanism Of Toxicity | Sterigmatocystin's carcinogenic properties are a result of its ability to form guanyl DNA adducts and bind to DNA. In addition, DNA adduct formation causes enhanced production of reactive oxygen species and an imbalance in antioxidant defense, leading to enhanced lipid peroxidation that causes cell damage. (A2888, A2958, A2959) |
Toxicity | LD50: 166 mg/kg (Rat, 10 days); LD50: >800 mg/kg (Mouse); LD50: 60-65 mg/kg (Intraperitoneal, Rat). |
Reference Reading
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2