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7220-81-7

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7220-81-7 Usage

Description

Aflatoxin B2 is a naturally occurring mycotoxin and food contaminant produced by various species of the mold Aspergillus. It is the dihydro derivative of aflatoxin B1 and belongs to the blue fluorescent family of bisfuranocoumarin mycotoxins. Aflatoxin B2 has a hexahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4, and 11. It is a likely pathogen that causes hepatocellular carcinoma and is highly carcinogenic. Aflatoxin B2 is found widely in nature in trace amounts, particularly in grains and nuts. It is an off-white powder and is one of the fungal metabolic products produced in food and feed contaminated by Aspergillus species.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 7220-81-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,2,2 and 0 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 7220-81:
(6*7)+(5*2)+(4*2)+(3*0)+(2*8)+(1*1)=77
77 % 10 = 7
So 7220-81-7 is a valid CAS Registry Number.

7220-81-7 Well-known Company Product Price

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  • Sigma-Aldrich

  • (ERMAC058)  AflatoxinB2solution  3.80 μg/g in acetonitrile, ERM® certified Reference Material

  • 7220-81-7

  • ERMAC058-4ML

  • 3,807.18CNY

  • Detail

7220-81-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name aflatoxin B2

1.2 Other means of identification

Product number -
Other names (6aR-cis)-2,3,6a,8,9,9a-hexahydro-4-methoxy-cyclopenta[c]furo[3',2',4,5]furo[2,3-h][1]benzopyran-1,11-dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7220-81-7 SDS

7220-81-7Synthetic route

(-)-2,3,3aS,8aR-tetrahydro-4-hydroxy-6-methoxy[2,3-d]-benzo[b]furan
6795-22-8

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

ethyl 2-bromo-5-oxocyclopent-1-enecarboxylate
30694-05-4

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

aflatoxin B2
7220-81-7

aflatoxin B2

Conditions
ConditionsYield
With sodium hydrogencarbonate; zinc(II) carbonate In dichloromethane at 20℃; for 20h;36%
aflatoxin B1
1162-65-8

aflatoxin B1

aflatoxin B2
7220-81-7

aflatoxin B2

Conditions
ConditionsYield
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

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

aflatoxin B2
7220-81-7

aflatoxin B2

Conditions
ConditionsYield
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

acetic acid 6-methoxy-5-trifluoromethanesulfonyloxy-2,3,3a,8a-tetrahydro-1,8-dioxa-cyclopenta[a]inden-4-yl ester

aflatoxin B2
7220-81-7

aflatoxin B2

Conditions
ConditionsYield
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

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

aflatoxin B2

Conditions
ConditionsYield
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

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

aflatoxin B2
7220-81-7

aflatoxin B2

Conditions
ConditionsYield
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

2-methoxy-1,4-benzoquinone

aflatoxin B2
7220-81-7

aflatoxin B2

Conditions
ConditionsYield
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

(-)-2,3,3aS,8aR-tetrahydro-5-hydroxy-6-methoxy[2,3-d]-benzo[b]furan

aflatoxin B2
7220-81-7

aflatoxin B2

Conditions
ConditionsYield
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

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

aflatoxin B2
7220-81-7

aflatoxin B2

Conditions
ConditionsYield
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

7220-81-7Downstream Products

7220-81-7Relevant articles and documents

Kinetic and mechanistic investigations on reductions of aflatoxins by lactic acid

Shukla, Ram S.,Verma, Ramtej J.,Mehta, Daxa N.

, p. 2737 - 2741 (2002)

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.

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