CAS 22897-08-1

5-Methoxysterigmatocystin

Description:

5-Methoxysterigmatocystin is a naturally occurring mycotoxin produced by certain species of fungi, particularly those in the Aspergillus genus. It is structurally related to sterigmatocystin, which is known for its potential carcinogenic properties. This compound features a methoxy group, which influences its chemical reactivity and biological activity. 5-Methoxysterigmatocystin is characterized by its complex polycyclic structure, which includes multiple fused rings, contributing to its stability and persistence in the environment. It is typically found in agricultural products and can pose health risks through exposure, particularly in contaminated food sources. The compound is of interest in toxicology and food safety due to its potential effects on human health, including its role as a mutagen and carcinogen. Analytical methods such as chromatography are often employed to detect and quantify this mycotoxin in various matrices. Understanding its characteristics is crucial for assessing risks and implementing safety measures in food production and storage.

Formula: C₁₉H₁₄O₇

InChI: InChI=1S/C19H14O7/c1-22-10-4-3-9(20)14-16(21)15-11(23-2)7-12-13(18(15)26-17(10)14)8-5-6-24-19(8)25-12/h3-8,19-20H,1-2H3/t8-,19+/m0/s1

InChI key: InChIKey=VVRUNWFPOWIBDY-WPCRTTGESA-N

SMILES: O(C)C=1C2=C(C=3[C@]4([C@@](OC3C1)(OC=C4)[H])[H])OC=5C(C2=O)=C(O)C=CC5OC

Synonyms:

• (3aR,12cS)-3a,12c-Dihydro-8-hydroxy-6,11-dimethoxy-7H-furo[3′,2′:4,5]furo[2,3-c]xanthen-7-one
• 5-Methoxysterigmatocystin
• 7H-Furo[3′,2′:4,5]furo[2,3-c]xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6,11-dimethoxy-, (3aR,12cS)-
• 7H-Furo[3′,2′:4,5]furo[2,3-c]xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6,11-dimethoxy-, (3aR-cis)-
• 7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6,11-dimethoxy-, (3aR,12cS)-
• (3aR,12cS)-8-Hydroxy-6,11-dimethoxy-3a,12c-dihydro-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one

5-Methoxysterigmatocystin

CAS: 22897-08-1

5-Methoxysterigmatocystin is a mycotoxin characterized by its cytotoxic and genotoxic properties. It exhibits cytotoxic effects on cancer cell lines A549 and HepG2, with IC50 values of 5.5 μM and 0.7 μM, respectively. Additionally, it induces DNA damage. 5-Methoxysterigmatocystin acts as a photosensitizer, generating singlet oxygen (1O2) under visible light.

Formula: C₁₉H₁₄O₇

Molecular weight: 354.31

Ref: TM-TN7877

5-Methoxysterigmatocystin

CAS: 22897-08-1

Formula: C₁₉H₁₄O₇

Molecular weight: 354.3

Ref: 7W-GL4839

5-Methoxysterigmatocystin

Controlled Product

CAS: 22897-08-1

Formula: C₁₉H₁₄O₇

Color and Shape: Neat

Molecular weight: 354.31

Ref: TR-M266998