1H,12H-Furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione, 3,4,7a,10a-tetrahydro-5-methoxy-, (7aR-cis)-

Base Information

• Chemical Name: 1H,12H-Furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione, 3,4,7a,10a-tetrahydro-5-methoxy-, (7aR-cis)-
• CAS No.: 1165-39-5
• Molecular Formula: C17H12O7
• Molecular Weight: 328.278
• Hs Code.: 29322090
• European Community (EC) Number: 214-615-9
• Metabolomics Workbench ID: 104965
• Wikidata: Q105343426
• Mol file: 1165-39-5.mol

Synonyms:aflatoxin G(1);aflatoxin G1

Chemical Property of 1H,12H-Furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione, 3,4,7a,10a-tetrahydro-5-methoxy-, (7aR-cis)-

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 244-246 °C
• Refractive Index: 1.4790 (estimate)
• Boiling Point: 612.083 °C at 760 mmHg
• Flash Point: 274.15 °C
• PSA: 84.20000
• Density: 1.596 g/cm³
• LogP: 1.86050
• Storage Temp.: 2-8°C
• Water Solubility.: 15mg/L(temperature not stated)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 328.05830272
• Heavy Atom Count: 24
• Complexity: 666

Purity/Quality:

98%,99%, ^*data from raw suppliers

Aflatoxin G1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,F,Xn
• Hazard Codes: T+,T,F,Xn
• Statements: 45-26/27/28-65-48/23/24/25-36/38-11-46-39/23/24/25-23/24/25-36-20/21/22
• Safety Statements: 53-28-36/37-45-62-26-16-7-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C2C3=C(C(=O)OCC3)C(=O)OC2=C4C5C=COC5OC4=C1
• Isomeric SMILES: COC1=C2C3=C(C(=O)OCC3)C(=O)OC2=C4[C@H]5C=CO[C@H]5OC4=C1
• Uses: Aflatoxins B1, B2, G1, G2 as secondary metabolites of fungal species such as Aspergillus flavus or Aspergillus parasiticus growing on a variety of foods (peanuts, nuts, spices, cereals). Aflatoxins a re a group of very carcinogenic mycotoxins with hepatotoxic effects. Aflatoxin G1 is the major analogue of the green fluorescent family of bisfuranocoumarin mycotoxins produced by Aspergillus flavus and related species. Alfatoxins are one of the most potent mycotoxins known but are in fact "pre-toxins", requiring metabolic activation to the toxic principle. Aflatoxins are found widely in nature in trace amounts, particularly in grains and nuts. The toxicity of these metabolites was first recognised in the 1950s and their structures elucidated in 1963. Aflatoxins have been extensively reviewed. Aflatoxin G1 from Aspergillus flavus has been used as a standard for the determination of aflatoxin in various samples.

Technology Process of 1H,12H-Furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione, 3,4,7a,10a-tetrahydro-5-methoxy-, (7aR-cis)-

There total 2 articles about 1H,12H-Furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione, 3,4,7a,10a-tetrahydro-5-methoxy-, (7aR-cis)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ aflatoxin-G1 (1165-39-5,13655-43-1,31272-49-8)

Guidance literature:

aus Verb. (42), Verb. (47);

DOI:10.1021/ja00732a032

Reference yield:

aflatoxin B1 (1162-65-8) → aflatoxin B1n exo/endo-8,9-epoxides (1165-39-5)

Guidance literature:

With 3,3-dimethyldioxirane;

DOI:10.1016/0165-1161(94)90030-2

Reference yield:

aflatoxin G1 (1165-39-5) → aflatoxin G2 (7241-98-7)

Guidance literature:

With hydrogenchloride; sodium hydroxide; LACTIC ACID; at 37 ℃; pH=3.35 - 4.50; Further Variations:; reagents concentration; Kinetics;

DOI:10.1016/S0960-894X(02)00533-4

upstream raw materials:

aflatoxin B₁

Downstream raw materials:

aflatoxin G₂

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.

Methoxymethyl-Directed Aryl Metalation. A Total Synthesis of (+/-)-Averufin

10.1021/ja00413a018

The research described in the scholarly article presents a total synthesis of (f)-averufin, a key intermediate in the biosynthesis of aflatoxin, a potent carcinogen produced by certain strains of the fungus Aspergillus. The purpose of this study was to develop a method for synthesizing averufin in its fully unprotected, bioactive form, which is challenging due to the tendency of its highly oxygenated aromatic rings to rearrange or decompose under acidic or basic conditions. The researchers successfully achieved this by employing methoxymethyl protecting groups, which allowed for regiospecific aryl metalation and the selective introduction of electrophiles to simple oxygenated benzenoid precursors. The synthesis involved the regiospecific coupling of the phthalide anion of 3b and the benzyne derived from aryl bromide 4 to form the anthraquinone 5c, the immediate precursor to averufin. The use of methoxymethyl groups was crucial for protecting and deprotecting hydroxyl functions under mild conditions, enabling the synthesis of averufin with high yields and selectivity.

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