Aflatoxin B2

Base Information

• Chemical Name: Aflatoxin B2
• CAS No.: 7220-81-7
• Molecular Formula: C17H14 O6
• Molecular Weight: 314.295
• Hs Code.: 29322090
• European Community (EC) Number: 230-618-8
• UNII: 7SKR7S646P
• DSSTox Substance ID: DTXSID70222535
• Nikkaji Number: J37.504G
• Wikidata: Q26840819
• Metabolomics Workbench ID: 56907
• Mol file: 7220-81-7.mol

Synonyms:aflatoxin B2;aflatoxin B2 alpha;aflatoxin B2, (6aR-cis)-isomer

Chemical Property of Aflatoxin B2

Chemical Property:

• Melting Point: 286-289 °C
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 521 °C at 760 mmHg
• Flash Point: 234 °C
• PSA: 74.97000
• Density: 1.52 g/cm³
• LogP: 2.15290
• Storage Temp.: 2-8°C
• Water Solubility.: 15mg/L(temperature not stated)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 314.07903816
• Heavy Atom Count: 23
• Complexity: 610

Purity/Quality:

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

Aflatoxin B2 ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Mycotoxins
• Canonical SMILES: COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C5CCOC5OC4=C1
• Isomeric SMILES: COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4[C@@H]5CCO[C@@H]5OC4=C1
• General Description: Aflatoxin B2 is a highly toxic and carcinogenic secondary metabolite produced by certain Aspergillus species, structurally related to Aflatoxin B1 but differing by the saturation of one double bond in the difuran ring system. It shares similar toxicological properties with other aflatoxins, including potent hepatotoxicity and carcinogenicity, and is a significant food safety concern due to its contamination of crops such as maize and peanuts. AFLATOXIN B2's complex structure, featuring a fused cyclopenta-furo-benzopyran core with methoxy and dihydro functionalities, poses challenges for chemical synthesis, though recent advances have demonstrated feasible synthetic routes via key intermediates.

Technology Process of Aflatoxin B2

There total 9 articles about Aflatoxin B2 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: 36.0%

(-)-2,3,3aS,8aR-tetrahydro-4-hydroxy-6-methoxy[2,3-d]-benzo[b]furan (6795-22-8) + ethyl 2-bromo-5-oxocyclopent-1-enecarboxylate (30694-05-4) → aflatoxin B2 (7220-81-7)

Guidance literature:

With sodium hydrogencarbonate; zinc(II) carbonate; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1021/ja054503m

Reference yield:

2-methoxy-1,4-benzoquinone (2880-58-2) → aflatoxin B2 (7220-81-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: (R)-α,α-diphenyl-2-pyrrolidinemethanol derived catalyst / acetonitrile / 5 h / 20 °C

2.1: AcOH / 48 h / 110 °C

2.2: 40 percent / aq. H₂SO₄ / 1 h / 75 °C

3.1: 80 percent / DMAP; pyridine / CH₂Cl₂ / 2 h / 0 °C

4.1: tetrahydrofuran; diethyl ether / 2 h / -20 °C

5.1: 162 mg / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

6.1: 62.5 percent / urea-H₂O₂ complex; trifluoroacetic anhydride / CH₂Cl₂ / 48 h / 20 °C

7.1: 60 percent / H₂; Raney nickel / methanol / 3 h / 20 °C

8.1: 36 percent / NaHCO₃; ZnCO₃ / CH₂Cl₂ / 20 h / 20 °C

With pyridine; dmap; (R)-α,α-diphenyl-2-pyrrolidinemethanol derived catalyst; hydrogen; urea hydrogen peroxide adduct; nickel; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; zinc(II) carbonate; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 5.1: Dess-Martin oxidation / 6.1: Baeyer-Villiger oxidation;

DOI:10.1021/ja054503m

Reference yield:

(-)-cis-5-trifluoromethanesulfonyloxy-2,3,3aS,8aR-tetrahydro-6-methoxy[2,3-d]-benzo[b]furan-4-carboxaldehyde (865811-99-0) → aflatoxin B2 (7220-81-7)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran; diethyl ether / 2 h / -20 °C

2: 162 mg / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

3: 62.5 percent / urea-H₂O₂ complex; trifluoroacetic anhydride / CH₂Cl₂ / 48 h / 20 °C

4: 60 percent / H₂; Raney nickel / methanol / 3 h / 20 °C

5: 36 percent / NaHCO₃; ZnCO₃ / CH₂Cl₂ / 20 h / 20 °C

With hydrogen; urea hydrogen peroxide adduct; nickel; sodium hydrogencarbonate; Dess-Martin periodane; zinc(II) carbonate; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2: Dess-Martin oxidation / 3: Baeyer-Villiger oxidation;

DOI:10.1021/ja054503m

upstream raw materials:

aflatoxin B₁

(-)-2,3,3aS,8aR-tetrahydro-4-hydroxy-6-methoxy[2,3-d]-benzo[b]furan

ethyl 2-bromo-5-oxocyclopent-1-enecarboxylate

(-)-cis-5-trifluoromethanesulfonyloxy-2,3,3aS,8aR-tetrahydro-6-methoxy[2,3-d]-benzo[b]furan-4-carboxaldehyde

Refernces

A Formal Synthesis of Aflatoxin B2

10.1039/c39880000721

This research aims to develop a synthetic route for Aflatoxin B2, a highly toxic and carcinogenic metabolite produced by various Aspergillus species. The study focuses on synthesizing a ring A differentiated tetrahydrofurobenzofuran intermediate, which can be converted into Aflatoxin B2. Key chemicals used in the research include 3,5-dimethoxy phenol, ortho-iodophenol, lead tetra-acetate (LTA), di-isobutylaluminum hydride (DIBAL-H), and t-butyl mercaptide. The researchers successfully synthesized the intermediate compound through a series of reactions, including iodination, reduction, and cyclization, achieving an overall yield of approximately 4%. The study concludes that the synthesized intermediate can be further converted into Aflatoxin B2, demonstrating a feasible synthetic pathway. The research also highlights the challenges in differentiating the oxygen substituents on ring A and presents a method to selectively demethylate the intermediate using t-butyl mercaptide, achieving improved selectivity and yield. This work represents a significant advancement in the synthesis of aflatoxins and lays the foundation for further studies on their structure and toxicity.

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