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β-Zearalenol

Cat No.:V29544 Purity: ≥98%
β-Zearalenol is a novel and potentnon-steroidal estrogenic mycotoxin isolated from Fusarium species.
β-Zearalenol
β-Zearalenol Chemical Structure CAS No.: 71030-11-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
β-Zearalenol is a novel and potent non-steroidal estrogenic mycotoxin isolated from Fusarium species. β-Zearalenol potentially influences transcription and effects gene expression on translational level.
β-Zearalenol (CAS 71030-11-0) is a mycotoxin belonging to the zearalenone family, produced by Fusarium species that contaminate cereals and animal feed. With a molecular formula of C₁₈H₂₄O₅ and a molecular weight of 320.38 g/mol, this compound is a reduced metabolite of zearalenone with potent estrogenic activity. β-Zearalenol is an agonist of estrogen receptor α (ERα) and increases the proliferation of MCF-7 cells that endogenously express ERα with an EC₅₀ of 8.49 nM. It is a notable estrogenic metabolite formed through the microbial transformation of zearalenone. The compound is a mycotoxin and secondary metabolite primarily produced by certain Fusarium species commonly found in cereal grains.
Biological Activity I Assay Protocols (From Reference)
Targets
β-Zearalenol targets the estrogen receptor α (ERα), acting as an agonist. By binding to and activating ERα, it mimics the effects of estrogen, leading to estrogenic responses such as increased cell proliferation in ERα-positive cells. It has an EC₅₀ of 8.49 nM for increasing the proliferation of MCF-7 cells that endogenously express ERα. Its potent estrogenic activity makes it a significant mycotoxin of concern for food safety and animal health. It may also interact with other estrogen receptors and signaling pathways.
ln Vitro
In vitro, β-Zearalenol is a potent agonist of ERα, with an EC₅₀ of 8.49 nM for increasing the proliferation of MCF-7 cells that endogenously express ERα. Its activity is typically assessed in cell-based proliferation assays using ERα-positive breast cancer cell lines such as MCF-7. The compound's estrogenic activity is confirmed by its ability to activate estrogen-responsive reporter genes. Its potency is compared to that of estradiol and other estrogenic compounds.
ln Vivo
In vivo, β-Zearalenol is a mycotoxin that can cause estrogenic effects in animals. Its potent estrogenic activity can lead to reproductive disorders in livestock, including infertility, reduced litter size, and other reproductive abnormalities. The compound is a concern for food safety due to its presence in contaminated cereals and animal feed. It is not used as a therapeutic agent.
Enzyme Assay
In vitro non-cell enzyme/receptor binding assays for β-Zearalenol involve measuring its binding affinity to ERα. Radioligand binding studies using purified ERα and a labeled ligand (e.g., [³H]estradiol) are used to determine its affinity. Its ability to activate ERα can be assessed in cell-free transcription assays. These assays provide quantitative data on the compound's interactions with its molecular target.
Cell Assay
In vitro cell-based assays for β-Zearalenol use ERα-positive breast cancer cell lines such as MCF-7. Cells are treated with varying concentrations of the compound, and cell proliferation is assessed using MTT or similar assays to determine the EC₅₀ of 8.49 nM. The compound's ability to activate estrogen-responsive genes is measured by qPCR or reporter gene assays. These studies help to characterize the compound's estrogenic activity and potency.
Animal Protocol
In vivo animal studies for β-Zearalenol are typically toxicological studies to assess its effects on reproductive function. Animals are exposed to the compound through contaminated feed, and parameters such as reproductive performance, hormone levels, and organ weights are assessed. Its estrogenic effects are evaluated by measuring uterine weight and other estrogen-responsive endpoints.
ADME/Pharmacokinetics
β-Zearalenol has a molecular weight of 320.38 g/mol and a molecular formula of C₁₈H₂₄O₅. It is a mycotoxin belonging to the zearalenone family. The compound should be stored under appropriate conditions, typically at -20°C, protected from light and moisture. Its stability in solution is good under proper storage conditions.
Toxicity/Toxicokinetics
β-Zearalenol is a mycotoxin with potent estrogenic activity. It can cause reproductive disorders in animals and is a concern for food safety. The compound is not intended for human or veterinary use. Standard laboratory safety precautions should be followed when handling the compound.
References

[1]. Influence of the mycotoxins alpha- and beta-zearalenol (ZOL) on regulators of cap-dependent translation control in pig endometrial cells. Reprod Toxicol. 2004 Dec;19(2):189-99.

[2]. Influence of the mycotoxins alpha- and beta-zearalenol (ZOL) on regulators of cap-dependent translation control in pig endometrial cells. Reprod Toxicol. 2004 Dec;19(2):189-99.

Additional Infomation
β-Zearabenol is a macrolide antibiotic.
β-Zearalenol is a mycotoxin belonging to the zearalenone family, produced by Fusarium species. It is an agonist of ERα and increases the proliferation of MCF-7 cells with an EC₅₀ of 8.49 nM. Not a therapeutic agent; a mycotoxin of concern for food safety.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H24O5
Molecular Weight
320.38016
Exact Mass
320.162
CAS #
71030-11-0
PubChem CID
6437352
Appearance
White to off-white solid powder
Density
1.174g/cm3
Boiling Point
599ºC at 760 mmHg
Melting Point
137-139ºC
Flash Point
217.9ºC
Index of Refraction
1.548
LogP
3.371
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
0
Heavy Atom Count
23
Complexity
408
Defined Atom Stereocenter Count
2
SMILES
C[C@H]1CCC[C@H](CCC/C=C/C2=C(C(=CC(=C2)O)O)C(=O)O1)O
InChi Key
FPQFYIAXQDXNOR-PMRAARRBSA-N
InChi Code
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
Chemical Name
(4S,8S,12E)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 100 mg/mL (~312.13 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.80 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (7.80 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.80 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.1213 mL 15.6065 mL 31.2129 mL
5 mM 0.6243 mL 3.1213 mL 6.2426 mL
10 mM 0.3121 mL 1.5606 mL 3.1213 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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