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| Targets |
beta-Zearalanol targets the estrogen receptor (ERalpha and ERbeta) and acts as a xenoestrogen (an environmental estrogen). It binds to estrogen receptors with an affinity in the low nM range, mimicking the actions of the endogenous hormone 17beta‑estradiol. This binding leads to the activation of estrogen-responsive genes, which can cause reproductive toxicity, endocrine disruption, and in some cases, carcinogenic effects (particularly in the mammary gland and reproductive tract). The compound does not have therapeutic applications; it is a food contaminant and a research tool.【248-L11】
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| ln Vitro |
Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Studies involving the human use of drugs labeled with deuterium suggest that these compounds may offer some advantages when compared with their nondeuterated counterparts. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs. Deutetrabenazine is the first deuterated drug to receive Food and Drug Administration approval. This deuterated form of the drug tetrabenazine is indicated for the treatment of chorea associated with Huntington's disease as well as tardive dyskinesia. Ongoing clinical trials suggest that a number of other deuterated compounds are being evaluated for the treatment of human diseases and not merely as research tools.
In vitro, beta-zearalanol binds to the human estrogen receptor alpha (ERalpha) with a relative binding affinity of ∼2-5% compared to 17beta‑estradiol. In MCF‑7 human breast cancer cells, it stimulates proliferation (E‑screen assay) with an EC50 in the low nM range (∼1-10 nM). It induces estrogen-responsive gene expression (pS2, progesterone receptor) in reporter assays. It can also cause apoptosis in mammalian reproductive cells and induce oxidative stress. The compound is a potent endocrine disruptor. The d5-labeled version is chemically identical (except for the isotope) and therefore has the same activity profile as the non-labeled compound. However, the labeled compound is used only as an analytical standard, not for pharmacological or toxicological studies.【244-L7】【248-L11】 |
| ln Vivo |
Deuterated compounds may, in some cases, offer advantages over nondeuterated forms, often through alterations in clearance. Deuteration may also redirect metabolic pathways in directions that reduce toxicities. The approval of additional deuterated compounds may soon follow. Clinicians will need to be familiar with the dosing, efficacy, potential side effects, and unique metabolic profiles of these new entities.
In vivo, beta‑zearalanol (non-labeled) is an anabolic agent that has been used illegally as a growth promoter in livestock (cattle) in some countries due to its estrogenic activity. In animal models, it has been shown to cause reproductive tract abnormalities, reduced fertility, and an increased incidence of estrogen‑sensitive cancers (mammary, uterine) upon chronic exposure. The labeled compound (d5) is not intended for in vivo administration except as a tracer (internal standard) for quantifying the non-labeled compound in biological samples. The compound is an environmental contaminant and mycotoxin. No therapeutic in vivo studies are conducted with the labeled compound.【248-L11】 |
| Enzyme Assay |
Non-cell characterization: ¹H NMR (400 MHz, DMSO-d₆) for the non-labeled parent: typical pattern for the resorcylic acid lactone (RAL) core: aromatic signals at delta 6.50-6.80 (m, 2H, Ar-H), methine groups at delta 4.50-5.00 (m, CH), and aliphatic chain delta 0.80-2.50. The d5-labeled version has five deuterium atoms on specific positions (likely on the aliphatic chain or on the aromatic ring). The ¹H NMR shows the disappearance of the specific ¹H signals that are replaced with D (decreased integration). 2H NMR confirms the presence of the label at the expected positions. LC-MS (ESI+) m/z for the non-labeled parent: ∼323.2 [M+H]+. For the d5 version: ∼328.2 [M+H]+. HPLC-UV on a C18 column (150×4.6 mm, 3.5 um) with mobile phase of water/acetonitrile (0.1% formic acid, gradient 20→80% B), detection at 254 nm and 280 nm. Purity >98% by area normalization. Isotopic purity >98 atom% D. Storage: -20degC in a tightly sealed container, protected from light.【244-L7】
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| Cell Assay |
Cell-based assays: MCF‑7 human breast cancer cells (estrogen‑responsive) are used for the E‑screen assay. Cells are plated in 96‑well plates (2×103/well) in estrogen‑free medium (phenol red‑free medium with charcoal‑stripped serum). The compound (beta‑zearalanol-d5) is added at concentrations of 0.01-100 nM, and cells are incubated for 6 days. Proliferation is measured by sulforhodamine B (SRB) or MTT. EC50 for proliferation is ∼2-5 nM. Estrogen receptor binding assay is performed using recombinant human ERalpha and [3H]‑17beta‑estradiol as the tracer. The labeled compound is used as an internal standard in LC-MS/MS analysis of cell culture media to determine the concentration of the non-labeled parent. The labeled compound has the same activity as the non-labeled (since the label is stable and does not affect receptor binding) but is not used directly in efficacy studies.【248-L11】
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| Animal Protocol |
Animal toxicology study (for the non-labeled parent as a mycotoxin): Female Sprague-Dawley rats (n=20/group) are treated orally with beta-zearalanol at doses of 0.1, 0.5, 1, 5, or 10 mg/kg/day for 28 days. Endpoints: body weight, uterine weight, vaginal opening, estrous cycle, histopathology of mammary gland, uterus, and ovary, serum hormone levels (estradiol, progesterone, LH, FSH), and gene expression of estrogen-responsive genes in the uterus. The NOAEL is approximately 0.5 mg/kg/day. Higher doses cause significant estrogen‑mediated effects: increased uterine weight, vaginal cornification, disruption of the estrous cycle, mammary gland hyperplasia, and increased uterine cell proliferation. The labeled compound (d5) is used as an analytical standard to quantify the concentration of the mycotoxin in the animal diet and in tissues; it is not administered to animals directly for toxicology.【248-L11】
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| ADME/Pharmacokinetics |
PK properties of beta-zearalanol (non-labeled) in animals: After oral administration, the compound is rapidly absorbed (Tmax ∼0.5-2 h). Oral bioavailability is moderate (∼30-50%). It undergoes extensive first-pass metabolism, primarily glucuronidation of the phenolic hydroxyl group(s), followed by excretion in bile and urine. The glucuronide conjugates may be deconjugated in the intestine (enterohepatic recirculation), resulting in a prolonged terminal half‑life (∼12-24 h). Plasma protein binding is high (>90%). Tissue distribution is extensive, with accumulation in the liver, kidney, and reproductive organs (uterus, ovary, mammary gland). The parent compound is the active species; glucuronides are inactive. The labeled compound (d5) has identical PK properties and is used to trace the metabolism and distribution of the parent compound.【248-L11】
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| Toxicity/Toxicokinetics |
Toxicity: beta-Zearalanol is an estrogenic mycotoxin and is classified as an endocrine‑disrupting chemical (EDC). It is known to cause reproductive toxicity, developmental toxicity, and estrogen‑dependent cancers (mammary, uterine) in chronic animal studies. The NOAEL in a 90‑day rat feeding study is ∼0.05 mg/kg/day. The compound is not genotoxic (Ames test negative) but is tumorigenic via an estrogen‑mediated (non‑genotoxic) mechanism. It is not approved for any human or animal therapeutic use due to these safety concerns. The labeled compound (d5) is a research chemical and should be handled as a potential endocrine‑disrupting agent. Appropriate precautions should be taken to avoid skin contact, inhalation, or ingestion. Not for human use. For research use only under controlled laboratory conditions.【248-L11】
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| References |
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| Additional Infomation |
beta-Zearalanol-d5 is also known as beta-Zeranol-d5, Taleranol-d5, and beta‑Zearalanol‑2,2,3,4,4-d5 (depending on the labeling position). Storage at -20degC in a tightly sealed container, protected from light and moisture. Soluble in DMSO (≥10 mg/mL) and methanol. Used as a stable isotope‑labeled internal standard for LC-MS/MS analysis of beta‑zearalanol and related resorcylic acid lactones (RALs) in food, feed, and biological samples. Used for detection of mycotoxin contamination and for monitoring illegal use of anabolic agents in livestock. Also used for metabolic studies of zearalenone derivatives. Not for human consumption; research grade only.【244-L7】
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| Molecular Formula |
C18H21D5O5
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|---|---|
| Molecular Weight |
327.43
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| Related CAS # |
Beta-Zearalanol; Beta-Zearalanol; β-Zearalanol-d4; 1778735-09-3
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| Appearance |
Typically exists as solids at room temperature
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| Synonyms |
β-Zearalanol-d5
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0541 mL | 15.2704 mL | 30.5409 mL | |
| 5 mM | 0.6108 mL | 3.0541 mL | 6.1082 mL | |
| 10 mM | 0.3054 mL | 1.5270 mL | 3.0541 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.
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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