Aflatoxin B1

Base Information

• Chemical Name: Aflatoxin B1
• CAS No.: 1162-65-8
• Deprecated CAS: 11003-08-0,13214-11-4,27261-02-5,13214-11-4,27261-02-5
• Molecular Formula: C17H12O6
• Molecular Weight: 312.279
• Hs Code.: 29322090
• European Community (EC) Number: 214-603-3
• NSC Number: 529592
• UN Number: 2811
• UNII: 9N2N2Y55MH
• DSSTox Substance ID: DTXSID9020035,DTXSID00873175
• Nikkaji Number: J5.139J
• Wikipedia: Aflatoxin_B1
• Wikidata: Q4689278
• NCI Thesaurus Code: C1315
• Metabolomics Workbench ID: 52937
• ChEMBL ID: CHEMBL1697694
• Mol file: 1162-65-8.mol

Synonyms:Aflatoxin B;Aflatoxin B(1);Aflatoxin B1;Aflatoxin B1 Dihydrochloride, (6aR-cis)-Isomer;Aflatoxin B1, (6aR-cis)-Isomer, 14C-Labeled;Aflatoxin B1, (6aR-cis)-Isomer, 2H-Labeled;Aflatoxin B1, (6aR-cis)-Isomer, 3H-Labeled;Aflatoxin B1, cis(+,-)-Isomer;HSDB 3453;HSDB-3453;HSDB3453;NSC 529592;NSC-529592;NSC529592

Chemical Property of Aflatoxin B1

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 3.05E-11mmHg at 25°C
• Melting Point: 268-269 °C
• Refractive Index: 1.686
• Boiling Point: 528.2°C at 760 mmHg
• Flash Point: 2 °C
• PSA: 74.97000
• Density: 1.56g/cm³
• LogP: 2.27650
• Storage Temp.: 2-8°C
• Water Solubility.: 15mg/L(temperature not stated)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 312.06338810
• Heavy Atom Count: 23
• Complexity: 650
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Aflatoxin B1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, T, Xn, F
• Hazard Codes: T+,T,Xn,F
• Statements: 45-46-26/27/28-36-20/21/22-11-65-48/23/24/25-36/38-39/23/24/25-23/24/25
• Safety Statements: 53-45-36-26-16-24-7-62-36/37-28

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Mycotoxins
• Canonical SMILES: COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C5C=COC5OC4=C1
• Isomeric SMILES: COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4[C@@H]5C=CO[C@@H]5OC4=C1
• Uses: Aflatoxin B1 is the major analogue of a family of bisfuranocoumarin mycotoxins produced by Aspergillus flavus and related species. Aflatoxin B1 exhibits a distinctive UV spectrum and blue fluorescence. Aflatoxins are among 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. Aflatoxin B1 is a carcinogenic compound that induces transversion of G to T at codon 249 of the p53 tumor suppressor gene. Aflatoxin B1 may be used as an internal standard when testing for aflatoxin contamination in food products.

Technology Process of Aflatoxin B1

There total 6 articles about Aflatoxin B1 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: 24.0%

aflatoxin B2a (17878-54-5,80008-86-2,109278-37-7) → aflatoxin B1 (1162-65-8)

Guidance literature:

aflatoxin B_2a; With acetic anhydride; acetic acid; at 20 ℃; for 20h;

In toluene; at 240 ℃; for 0.25h; Further stages.;

DOI:10.1021/ja020988s

Reference yield:

norsolorinic acid (10254-99-6) → aflatoxin B1 (1162-65-8)

Guidance literature:

With metabolite-free SU-1 cell-free extract; S-Adenosylmethionine; NADPH; flavin adenine dinucleotide; In water; at 30 ℃; for 8h;

DOI:10.1021/ja974367o

Reference yield:

O-methylsterigmatocystin (30361-73-0,17878-69-2) → aflatoxin B1 (1162-65-8)

Guidance literature:

With NADPH; In acetone; at 37 ℃; for 84h; cell free extract of the Aspergillus parasiticus mutant AVN-1 (ATCC 56774);

DOI:10.1021/jo00095a016

upstream raw materials:

O-methylsterigmatocystin

norsolorinic acid

aflatoxin B_2a

sterigmatocystin

Downstream raw materials:

Aflatoxin B₁ 8,9-epoxide

alfatoxin B_2a

050668-79-6

<6aS-(6aα,8bβ,9α,9aα)>-8-(2-amino-1,6-dihydro-6-oxo-7H-purin-7-yl)-2,3-6a,8,9,9a-hexahydro-9-hydroxy-4-methoxycyclopentafuro<3',2':4,5>furo<2,3-h><1>benzopyran-1,11-dione

Refernces

The timing of aromatic deoxygenation in aflatoxin biosynthesis

10.1021/ja00203a057

The research investigates the timing of aromatic deoxygenation in aflatoxin biosynthesis and the partitioning between tetrahydro- and dihydrobisfuran formation in this process. The purpose is to understand the specific steps and intermediates involved in the biosynthesis of aflatoxin B1, a toxic compound produced by certain fungi. Key chemicals used in the research include versicolorin A, 6-deoxyversicolorin A, and various labeled compounds such as [9-13C]versicolorin A. The researchers used cell-free systems and in vivo experiments with fungal cultures to study the conversion of these compounds into aflatoxin B1. The conclusions indicate that versicolorin A efficiently incorporates into aflatoxin B1, while 6-deoxyversicolorin A does not, suggesting that the deoxygenation process does not occur through direct reduction of versicolorin A. Additionally, the research shows that the partitioning between tetrahydro- and dihydrobisfuran formation occurs at the point of versicolorin B formation, highlighting the pivotal role of versicolorin B in the biosynthetic pathway.