All Photos(4)

A6636

Sigma-Aldrich

Aflatoxin B1 from Aspergillus flavus

greener alternative

from Aspergillus flavus

Empirical Formula (Hill Notation):
C17H12O6
CAS Number:
Molecular Weight:
312.27
Beilstein:
1269174
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

Aspergillus flavus

assay

≥98.0% (HPLC)

greener alternative product score

old score: 35
new score: 11
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greener alternative product characteristics

Less Hazardous Chemical Syntheses
Safer Solvents and Auxiliaries
Inherently Safer Chemistry for Accident Prevention
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greener alternative category

Re-engineered

storage temp.

2-8°C

SMILES string

COc1cc2OC3OC=CC3c2c4OC(=O)C5=C(CCC5=O)c14

InChI

1S/C17H12O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8,17H,2-3H2,1H3/t8-,17+/m0/s1

InChI key

OQIQSTLJSLGHID-WNWIJWBNSA-N

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Application

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.

Biochem/physiol Actions

Aflatoxin B1 is a carcinogenic compound produced by Aspergillus flavus, a common soil fungus, that induces transversion of G to T at codon 249 of the p53 tumor suppressor gene. Aflatoxin B1 is a food contaminant and a hepatocarcinogen. Aflatoxin is biotransformed to genotoxic intermediates by P450 Phase I enzymes, mainly CYP3A4 via aflatoxin B1 3-hydroxylation. Detoxification depends on Phase II enzymes, such as Glutathione S-Transferase and AFB(1)-aldehyde reductase (AFAR). Aflatoxin B1 is a CYP1A2, CYP2A6, CYP2D6, and CYP3A family substrate.

Warning

Possibly carcinogenic.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A6636.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Oral - Acute Tox. 2 Inhalation - Carc. 1B - Muta. 1B - Repr. 2

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Hajar Zolfaghari et al.
Advanced pharmaceutical bulletin, 10(3), 482-487 (2020-07-16)
Purpose: The present study was conducted to assess the ability of probiotic bacteria and yeasts strains to reduce aflatoxin B1 (AFB1) in gastrointestinal simulated conditions. Aflatoxins are potent carcinogenic and immunosuppressive agents. Acute exposure to a high level of aflatoxins...
Ilenia Siciliano et al.
Toxins, 7(3), 743-754 (2015-03-10)
Fungi belonging to the genus Alternaria are common pathogens of fruit and vegetables with some species able to produce secondary metabolites dangerous to human health. Twenty-eight Alternaria isolates from rocket and cabbage were investigated for their mycotoxin production. Five different...
S Piekkola et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 29(6), 962-971 (2012-03-02)
Mycotoxins such as the aflatoxins and deoxynivalenol (DON) are frequent contaminants of food. Aflatoxin B1 (AFB1) and DON affect the immune system and restrict growth; additionally AFB1 is carcinogenic. To date there are limited descriptive biomarker data concerning maternal exposures...
Sharaf S Omar et al.
Foods (Basel, Switzerland), 9(5) (2020-05-24)
In Jordan as in other worldwide countries, mycotoxins are considered a serious national problem in food supplies. As a result, almost all nations are setting and adopting different regulations targeting the control of mycotoxins levels in the domestic food supply...
Agnieszka Chlebicz et al.
Probiotics and antimicrobial proteins, 12(1), 289-301 (2019-02-06)
The aim of the following research was to determine the detoxification properties of probiotic Lactobacillus sp. bacteria (12 strains) and S. cerevisiae yeast (6 strains) towards mycotoxins, such as aflatoxin B1, deoxynivalenol, fumonisins, T-2 toxin and zearalenone, which pose as...

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