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7220-81-7

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7220-81-7 Usage

Chemical Properties

off-white powder

Uses

Different sources of media describe the Uses of 7220-81-7 differently. You can refer to the following data:
1. 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]
2. 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.

Definition

ChEBI: An aflatoxin having a hexahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.

General Description

Aflatoxin B2 is one of the fungal metabolic products produced in food and feed, contaminated by?Aspergillus?species.

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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