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Fusarium toxin

HCID 5375083
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
17924-92-4
Standard SMILES
CC1CCCC(=O)CCC/C=C/c2cc(O)cc(O)c2C(=O)O1
InChIKey
MBMQEIFVQACCCH-CLTKARDFSA-N
Molecular formula
C18H22O5
Average molar mass
318.4 g/mol
Monoisotopic mass
318.1467238

Overview

(S,E)-Zearalenone is a macrolide and a member of resorcinols.

Names & identifiers

Preferred name
Fusarium toxin
IUPAC
(12E)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione
English name
(E)-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione
Molecular weight
0

Names & synonyms

7645-23-0RefChem:1085627Fusarium toxin(S,E)-Zearalenone(12E)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dioneMycotoxin F-2Toxin, fusarium(E)-3,4,5,6,7,8,9,10-Octahydro-14,16-dihydroxy-3-methyl-7-oxo-1H-2-benzoxacyclotetradecin-1-oneSCHEMBL588841orb12202956-(10-Hydroxy-6-oxo-trans-1-undecenyl)-.beta.-resorcylic acid lactoneCHEMBL1397216
Show more names
(E)-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione
CHEBI:125462CHEBI:175078MBMQEIFVQACCCH-XVNBXDOJSA-N(11S)-11-methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione(S,E)-14,16-Dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-benzo[c][1]oxacyclotetradecine-1,7(8H)-dioneNCGC00095344-01NCGC00095344-03AB01209588-01

Database identifiers

CAS
17924-92-4、7645-23-0

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
83.8 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
0
Heavy atoms
23
Formal charge
0
Complexity
445

Experimental & physicochemical properties

Melting Point164 - 165 °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

Health Effects · 1 item

Zearalenone is a reproductive toxin and has been shown to cause infertility, abortion or other breeding problems in livestock. In humans it can cause earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia, and breast cancer in women. Zearalenone is also immunotoxic, genotoxic, and can cause kidney and liver damage. (L1947, A2960)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 item

Zearalenone's genotoxicity results from it's ability to cause DNA fragmentation, chromosome aberrations, and DNA adduct formation. It exerts cytotoxic effects by enhancing lipid peroxidation, increasing oxidative stress, and inducing apoptosis. Zearalenone also has significant estrogenic activity, causing severe reproductive problems in animals. In humans, Zearalenone has been shown to cause an earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia and breast cancer in women. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (A2960, A3014)

Carcinogen Classification3, not classifiable as to its carcinogenicity to humans. (L135)
Toxicity DataLD50: >2000 mg/kg (Oral, Mouse) (L1912) LD50: >500 mg/kg (Intraperitoneal, Mouse) (L1912)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Zearalenone is rapidly absorbed after oral administration. In humans, most of the zearalenone absorbed is not metabolized. The main metabolites include alpha- and beta-zeralenol, and the glucuronide conjugates of both the parent compound and its metabolites. Zearalenone and its metabolites are excreted mainly in the bile. (A741, L1912)

Cellular LocationsMembrane

Uses & manufacturing

Uses · 1 item

Zearalenone (ZEA), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Giberella species. Several Fusarium species also produce zearalenone as their primary toxin. It can be found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum, and also in bread. (L1947)

Additional notes

DefinitionChEBI: (S,E)-Zearalenone is a member of resorcinols and a macrolide.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
5375083
ChEMBL
CHEMBL1397216
ChEBI
CHEBI:175078
Nikkaji
J108.495J