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Aflatoxin B2 alpha

HCID 23648
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Basic information

CAS
22040-96-6
Standard SMILES
COc1cc2c(c3oc(=O)c4c(c13)CCC4=O)C1CCOC1O2
InChIKey
WWSYXEZEXMQWHT-UHFFFAOYSA-N
Molecular formula
C17H14O6
Average molar mass
314.29 g/mol
Monoisotopic mass
314.07903816

Overview

Aflatoxin B2 alpha is a member of coumarins.

Names & identifiers

Preferred name
Aflatoxin B2 alpha
IUPAC
11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,9,11,13(17)-tetraene-16,18-dione
English name
aflatoxin B2
Molecular formula
C17H14O6
Molecular weight
314.28946

Names & synonyms

Aflatoxin B2 alpha22040-96-611-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,9,11,13(17)-tetraene-16,18-dione11-methoxy-6,8,19-trioxapentacyclo(10.7.0.02,9.03,7.013,17)nonadeca-1,9,11,13(17)-tetraene-16,18-dioneRefChem:915226Dihydroafflatoxin B1orb321388SCHEMBL621001SCHEMBL29838910DTXSID10871940CHEBI:181914WWSYXEZEXMQWHT-UHFFFAOYSA-N
Show more names
Cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione, 2,3,6a.alpha.,8,9,9a.alpha.-hexahydro-4-methoxy-NS000027524-Methoxy-2,3,6a,8,9,9a-hexahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dioneCyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione, 2,3,6a,8,9,9a-hexahydro-4-methoxy-

Database identifiers

CAS
22040-96-6、7220-81-7
PubChem CID
23648
DTXSID
DTXSID10871940
ChEBI
CHEBI:181914
Nikkaji
J3.035.013H

Properties

Computed structural properties

XLogP
1.3
Topological polar surface area
71.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
1
Heavy atoms
23
Formal charge
0
Complexity
610

Experimental & physicochemical properties

Melting Point310 °C
Physical DescriptionSolid

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Treatment · 1 item

Administration of phonobarbital enhances hepatic transformation activities and also protects against AFB-induced toxicity, carcinogenicity and DNA binding in vivo. In cases of ingestion, feeding large quantities of an adsorbent such as activated charcoal may be used. Antioxidants such as ellagic acid and inducers of some cytochromes P450, such as indole-3-carbinol, may give a protective effect. (A704, L1879)

Health Effects · 1 item

The main target organ in mammals is the liver so aflatoxicosis is primarily a hepatic disease. Protracted exposure to aflatoxins may cause liver damage and necrosis, cholestasis, and hepatomas. Moreover, protracted exposure to aflatoxins has been associated with hepatocellular carcinoma, acute hepatitis, Reye's syndrome, bile duct cell proliferation, periportal fibrosis, hemorrhages, mucous membrane jaundice, fatty liver changes, cirrhosis in malnourished children, and kwashiorkor. However, aflatoxins accumulate in the presence of liver disease, and the association with hepatic cancer is confounded by the occurrence of hepatitis-B. Thus, it is not clear in these various instances whether aflatoxin is a primary cause of the disease, is an innocent bystander which accumulates secondary to the disease process, or is a contributing cause in conjunction with other factors. It is also mutagenic and teratogenic. Inhaled aflatoxins may produce pulmonary adenomatosis. Aflatoxins modify the immune system by affecting antibody formation, complement, cell-mediated immunity, and phagocytosis. (A704, L1956) Furocoumarins can cause photosensitization dermatitis especially if these compounds come into contact with the skin. Some furocoumarins, especially bifunctional furocoumarins, are known to be carcinogenic (A15105). Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs. Limited evidence of carcinogenic effect. (L579)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)

Chemistry & industry

Pharmacology

Metabolism/MetabolitesAflatoxin B2 is metabolized in the liver by microsomal monooxygenases to the less toxic reactive metabolite alfatoxin M2. Aflatoxin B2 is also proposed to be metabolized to B1, which in turn is transformed to M1. (A705, L1956)
Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 1 item

The native habitat of Aspergillus is in soil, decaying vegetation, hay, and grains undergoing microbiological deterioration and it invades all types of organic substrates whenever conditions are favorable for its growth. Crops which are frequently affected include cereals (maize, sorghum, pearl millet, rice, wheat), oilseeds (peanut, soybean, sunflower, cotton), spices (chile peppers, black pepper, coriander, turmeric, ginger), and tree nuts (almond, pistachio, walnut, coconut, brazil nut). The toxin can also be found in the milk of animals which are fed contaminated feed. Thus, aflatoxins are usually encountered in thecontext of chronic exposure, via food intake or secondary to the handling of foodstuffs. (L1956)

Additional notes

DefinitionChEBI: Aflatoxin B2 alpha is a member of coumarins.

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Compound notes

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Toxicity Summary · 1 item

Aflatoxins produce singlet oxygen upon their exposure to UV (365-nm) light. Singlet oxygen in turn activates them to mutagens and DNA binding species. Aflatoxin metabolites can intercalate into DNA and alkylate the bases through their epoxide moiety, binding particularity to N7-guanine bases. In addition to randomly mutating DNA, this is thought to cause mutations in the p53 gene, an important gene in preventing cell cycle progression when there are DNA mutations, or signaling apoptosis. (L1877, A2859, A2972) The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. (L579)

Signs and SymptomsA broad range of symptoms can be found depending upon dosage, including, vomiting, abdominal pain, hemorrhage, and pulmonary edema. (L1879)
Carcinogen Classification1, carcinogenic to humans (L135)