7220-81-7

Basic information

• Product Name: AFLATOXIN B2
• Synonyms: AFLATOXIN B2;(6ar-cis)-hexahydro-4-methoxy;,9,9a-alpha-hexahydro-4-methoxy-;2,3,6aalpha,8,9,9aalpha-hexahydro-4-methoxycyclopenta(c)furo(3’,2’:4,5)furo(2,;3-h)(1)benzopyran-1,11-dione;4-Methoxy-2,3,6a,8,9,9a-hexahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-H]chromene-1,11-dione;9aalpha-hexahydro-4-methoxy-;cyclopenta(c)furo(3’,2’:4,5)furo(2,3-h)(1)benzopyran-1,11-dione,2,3,6a-alpha,8
• CAS NO: 7220-81-7
• Molecular Formula: C17H14O6
• Molecular Weight: 314.29
• EINECS: 230-618-8
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;antibiotic;Biotoxins;Mycotoxins;Single component solutions;Cancer Research;CarcinogensCell Signaling and Neuroscience;Mold;Toxins and Venoms;CRM&Matrix RMApplication CRMs;A;AA to ALBiotoxins;Alphabetic;Food and Agriculture CRM;Other
• Mol File: 7220-81-7.mol

Chemical Properties

• Melting Point: 286-289 °C
• Boiling Point: 373.98°C (rough estimate)
• Flash Point: 11 °C
• Appearance: /
• Density: 1.2564 (rough estimate)
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: 15mg/L(temperature not stated)
• Merck: 13,180
• BRN: 1355115
• CAS DataBase Reference: AFLATOXIN B2(CAS DataBase Reference)
• NIST Chemistry Reference: AFLATOXIN B2(7220-81-7)
• EPA Substance Registry System: AFLATOXIN B2(7220-81-7)

Safety Data

• 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
• RIDADR: UN 3462 6.1/PG 1
• WGK Germany: 3
• RTECS: GY1722000
• F: 10
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 7220-81-7(Hazardous Substances Data)

Usage

Uses

Aflatoxin B2 is primarily known for its harmful effects on human and animal health, and its presence in food and feed is a major concern for food safety. However, it can be used in research and analysis for the following purposes:
Used in Research and Analysis:
Aflatoxin B2 is used as a reference compound for studying the toxic effects of mycotoxins on human and animal health. It helps in understanding the mechanisms of carcinogenesis and the role of aflatoxins in hepatocellular carcinoma.
Used in Food Safety Testing:
Aflatoxin B2 is used as an analytical standard for the development and validation of methods to detect and quantify aflatoxins in food and feed products. This helps in ensuring the safety and quality of food products and preventing the consumption of contaminated food.
Used in Environmental Monitoring:
Aflatoxin B2 can be used as an indicator of mold contamination in the environment, particularly in grains and nuts. Monitoring the presence of aflatoxins can help in assessing the risk of mycotoxin exposure and implementing preventive measures to reduce contamination.
Used in Agricultural Practices:
Aflatoxin B2 can be used to study the factors that contribute to mold growth and aflatoxin production in crops. This knowledge can help in developing strategies to minimize mold contamination and reduce the risk of aflatoxin exposure in agricultural products.

Safety Profile

Confirmed human carcinogen with experimental tumorigenic data. Poison by ingestion. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes. See also various aflatoxins.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Synthetic route

(-)-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)

Conditions	Yield
With sodium hydrogencarbonate; zinc(II) carbonate In dichloromethane at 20℃; for 20h;	36%

aflatoxin B1 (1162-65-8) → aflatoxin B2 (7220-81-7)

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

(-)-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)

Conditions	Yield
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 View Scheme

acetic acid 6-methoxy-5-trifluoromethanesulfonyloxy-2,3,3a,8a-tetrahydro-1,8-dioxa-cyclopenta[a]inden-4-yl ester (865812-13-1) → aflatoxin B2 (7220-81-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / H2; Raney nickel / methanol / 3 h / 20 °C 2: 36 percent / NaHCO3; ZnCO3 / CH2Cl2 / 20 h / 20 °C View Scheme

trifluoro-methanesulfonic acid 4-(1-hydroxy-ethyl)-6-methoxy-2,3,3a,8a-tetrahydro-1,8-dioxa-cyclopenta[a]inden-5-yl ester → aflatoxin B2 (7220-81-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 162 mg / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C 2: 62.5 percent / urea-H2O2 complex; trifluoroacetic anhydride / CH2Cl2 / 48 h / 20 °C 3: 60 percent / H2; Raney nickel / methanol / 3 h / 20 °C 4: 36 percent / NaHCO3; ZnCO3 / CH2Cl2 / 20 h / 20 °C View Scheme

(-)-cis-5-trifluoromethanesulfonyloxy-2,3,3aS,8aR-tetrahydro-4-acetyl-6-methoxy[2,3-d]-benzo[b]furan (865812-00-6) → aflatoxin B2 (7220-81-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 62.5 percent / urea-H2O2 complex; trifluoroacetic anhydride / CH2Cl2 / 48 h / 20 °C 2: 60 percent / H2; Raney nickel / methanol / 3 h / 20 °C 3: 36 percent / NaHCO3; ZnCO3 / CH2Cl2 / 20 h / 20 °C View Scheme

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

Conditions	Yield
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 View Scheme
Multi-step reaction with 8 steps 1.1: (R)-α,α-diphenyl-2-pyrrolidinemethanol derived catalyst / acetonitrile; CH2Cl2 / 10 h / -78 - 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 View Scheme

(-)-2,3,3aS,8aR-tetrahydro-5-hydroxy-6-methoxy[2,3-d]-benzo[b]furan (292824-29-4) → aflatoxin B2 (7220-81-7)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: AcOH / 48 h / 110 °C 1.2: 40 percent / aq. H2SO4 / 1 h / 75 °C 2.1: 80 percent / DMAP; pyridine / CH2Cl2 / 2 h / 0 °C 3.1: tetrahydrofuran; diethyl ether / 2 h / -20 °C 4.1: 162 mg / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C 5.1: 62.5 percent / urea-H2O2 complex; trifluoroacetic anhydride / CH2Cl2 / 48 h / 20 °C 6.1: 60 percent / H2; Raney nickel / methanol / 3 h / 20 °C 7.1: 36 percent / NaHCO3; ZnCO3 / CH2Cl2 / 20 h / 20 °C View Scheme

(-)-2,3,3aS,8aR-tetrahydro-5-hydroxy-6-methoxy[2,3-d]-benzo[b]furan-4-carboxaldehyde (292824-31-8) → aflatoxin B2 (7220-81-7)

Conditions

Yield

Multi-step reaction with 6 steps 1: 80 percent / DMAP; pyridine / CH2Cl2 / 2 h / 0 °C 2: tetrahydrofuran; diethyl ether / 2 h / -20 °C 3: 162 mg / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C 4: 62.5 percent / urea-H2O2 complex; trifluoroacetic anhydride / CH2Cl2 / 48 h / 20 °C 5: 60 percent / H2; Raney nickel / methanol / 3 h / 20 °C 6: 36 percent / NaHCO3; ZnCO3 / CH2Cl2 / 20 h / 20 °C View Scheme

Upstream product

• 1162-65-8 aflatoxin B₁ 
• 6795-22-8 (-)-2,3,3aS,8aR-tetrahydro-4-hydroxy-6-methoxy[2,3-d]-benzo[b]furan 
• 30694-05-4 ethyl 2-bromo-5-oxocyclopent-1-enecarboxylate 
• 865811-99-0 (-)-cis-5-trifluoromethanesulfonyloxy-2,3,3aS,8aR-tetrahydro-6-methoxy[2,3-d]-benzo[b]furan-4-carboxaldehyde 
• 865812-13-1 acetic acid 6-methoxy-5-trifluoromethanesulfonyloxy-2,3,3a,8a-tetrahydro-1,8-dioxa-cyclopenta[a]inden-4-yl ester 
• 865812-00-6 (-)-cis-5-trifluoromethanesulfonyloxy-2,3,3aS,8aR-tetrahydro-4-acetyl-6-methoxy[2,3-d]-benzo[b]furan 
• 2880-58-2 2-methoxy-1,4-benzoquinone 
• 292824-29-4 (-)-2,3,3aS,8aR-tetrahydro-5-hydroxy-6-methoxy[2,3-d]-benzo[b]furan 
• 292824-31-8 (-)-2,3,3aS,8aR-tetrahydro-5-hydroxy-6-methoxy[2,3-d]-benzo[b]furan-4-carboxaldehyde 

Relevant articles and documents

Kinetic and mechanistic investigations on reductions of aflatoxins by lactic acid

The kinetics of reduction of AFB1 to AFB2 and AFG1 to AFG2 by lactic acid has been investigated in dilute aqueous acidic solutions (pH 3.35-4.50) as a function of the concentrations of lactic acid, AFB1, AFG1 and hydrogen ion at 37°C. The rate of the reaction was found to be first order with respect to the concentrations of lactic acid and aflatoxins and independent on hydrogen ion concentration. The experimental results are interpreted in terms of mechanisms involving an initial formation of transient oxonium intermediate, which tends to polarize the olefinic (C=C) carbon, which in turn causes the hydride abstraction from α-carbon atom of lactic acid in rate determining step. The proposed mechanisms involve an overall transfer of two protons and two electrons from lactic acid to AFB1 and AFG1 to give the corresponding reduced less toxic products AFB2 and AFG2 and the oxidised product pyruvic acid.

Short, enantioselective total synthesis of aflatoxin B2 using an asymmetric [3+2]-cycloaddition step

A highly enantioselective [3+2]-cycloaddition reaction of 2,3-dihydrofuran with 1,4-benzoquinones using a chiral oxazaborolidinium triflimidate as catalyst has been developed which allows rapid access to a variety of chiral phenolic tricycles (enantiomeric excesses ranging from 91 to 98%). The utility of this new methodology is demonstrated by a short synthesis of the important pentacyclic natural product, aflatoxin B2. This exploratory study indicates that an even broader application of these catalysts to enantioselective cycloadditions may be possible. Copyright