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
• Uses: Aflatoxins are naturally occuring mycotoxins produced by various species of the mold Aspergillus, which can be found in legumes, corn, soybeans, rice, milk, and cheese. They are highly carcinogenic substances that are metabolized by the liver to a reactive epoxide intermediate, which produces adducts that modify DNA. Aflatoxin B1 induces transversion of G to T at codon 249 of the p53 tumor suppressor gene. This transversion is common in hepatocellular carcinoma patients living in regions with high levels of aflatoxin contamination. Aflatoxin B2 is the dihydro derivative of aflatoxin B1, a naturally occuring mycotoxin and food contaminant that is a likely pathogen that causes hepatocellular carcinoma.[Cayman Chemical] Aflatoxin B2 is the minor analogue of the blue 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.

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

• 1、 Zhou, Gang,Corey. "Short, enantioselective total synthesis of aflatoxin B2 using an asymmetric [3+2]-cycloaddition step". . p. 11958 - 11959. Retrieved 2007/10/03.