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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O5
Molecular Weight 320.3802
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .BETA.-ZEARALENOL

SMILES

C[C@H]1CCC[C@@H](O)CCC\C=C\C2=C(C(O)=CC(O)=C2)C(=O)O1

InChI

InChIKey=FPQFYIAXQDXNOR-PMRAARRBSA-N
InChI=1S/C18H24O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,14,19-21H,2,4-6,8-9H2,1H3/b7-3+/t12-,14-/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H24O5
Molecular Weight 320.3802
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

β-Zearalenol is a nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in Fusarium spp. β-Zearalenol is the β epimer of α-zearalenol and along with α-zearalenol is a major metabolite of zearalenone formed mainly in the liver but also to a lesser extent in the intestines during the first-pass metabolism. β-Zearalenol is about the same or slightly less potent as an estrogen relative to zearalenone. Contamination of grains by Fusarium species, notably maize, gives rise to high levels of zearalenol and is regarded as an important food quality issue for both human and animal health.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
11.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Cytotoxicity assay against African green monkey kidney fibroblast (Vero) cells was performed in triplicate employing the colorimetric method. Cells were grown in culture flasks or, for experiments, multiwell plates (TPP, Winiger, Wohlen, Switzerland) in DMEM/F12 1:1 medium (Life Technologies, Basel, Swit-zerland) supplemented with 5% fetal calf serum (FCS) (Sera-Tech) and incubated at 37°C in a humidified 5% CO2 atmosphere. Twice a week, cells were detached by treat-ment with trypsin-EDTA (Life Technologies), counted, and subcultured at ratios between 1:5 and 1:20. Cell samples were counted in duplicate and viability was determined using the trypan blue exclusion method.
Substance Class Chemical
Record UNII
35E809PP7O
Record Status Validated (UNII)
Record Version