4,6,8-Trihydroxy-3a,12a-dihydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione

Base Information

• Chemical Name: 4,6,8-Trihydroxy-3a,12a-dihydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione
• CAS No.: 6807-96-1
• Molecular Formula: C18H10 O7
• Molecular Weight: 338.28
• Hs Code.: 2932999099
• NSC Number: 274542
• DSSTox Substance ID: DTXSID30987517
• Mol file: 6807-96-1.mol

Synonyms:4,6,8-Trihydroxy-3a,12a-dihydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione;NSC-274542;SCHEMBL23199014;DTXSID30987517;NSC274542;Anthra[2,2-d]furan-5,10-dione, 3a,12a-dihydro-4,6,8-trihydroxy-, (3aS-cis)-

Chemical Property of 4,6,8-Trihydroxy-3a,12a-dihydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione

Chemical Property:

• Vapor Pressure: 1.14E-15mmHg at 25°C
• Melting Point: 289°C (rough estimate)
• Refractive Index: 1.6380 (estimate)
• Boiling Point: 614°C at 760 mmHg
• Flash Point: 233°C
• PSA: 113.29000
• Density: 1.752g/cm³
• LogP: 1.92480
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 338.04265265
• Heavy Atom Count: 25
• Complexity: 645

Purity/Quality:

VERSICOLORIN A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=COC2C1C3=C(O2)C=C4C(=C3O)C(=O)C5=C(C4=O)C=C(C=C5O)O
• General Description: Versicolorin A is a key intermediate in the aflatoxin B1 biosynthetic pathway, efficiently incorporated into aflatoxin B1 but not directly deoxygenated to form 6-deoxyversicolorin A, indicating that aromatic deoxygenation occurs at a later stage. Its role is pivotal in partitioning between tetrahydro- and dihydrobisfuran formation during the biosynthesis process, with versicolorin B serving as a critical branching point.

Refernces

The timing of aromatic deoxygenation in aflatoxin biosynthesis

10.1021/ja00203a057

The research investigates the timing of aromatic deoxygenation in aflatoxin biosynthesis and the partitioning between tetrahydro- and dihydrobisfuran formation in this process. The purpose is to understand the specific steps and intermediates involved in the biosynthesis of aflatoxin B1, a toxic compound produced by certain fungi. Key chemicals used in the research include versicolorin A, 6-deoxyversicolorin A, and various labeled compounds such as [9-13C]versicolorin A. The researchers used cell-free systems and in vivo experiments with fungal cultures to study the conversion of these compounds into aflatoxin B1. The conclusions indicate that versicolorin A efficiently incorporates into aflatoxin B1, while 6-deoxyversicolorin A does not, suggesting that the deoxygenation process does not occur through direct reduction of versicolorin A. Additionally, the research shows that the partitioning between tetrahydro- and dihydrobisfuran formation occurs at the point of versicolorin B formation, highlighting the pivotal role of versicolorin B in the biosynthetic pathway.