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| 1mg |
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| Other Sizes |
| Targets |
3-Chlorobisphenol A is an endocrine disruptor that targets the estrogen receptor (ER). It binds to both estrogen receptor alpha (ERalpha) and estrogen receptor beta (ERbeta), disrupting normal hormonal signaling pathways. It is an estrogenic compound, acting as a weak estrogen agonist. It also binds to the aryl hydrocarbon receptor (AhR), inducing the expression of xenobiotic-metabolizing enzymes such as CYP1A1. It may also interact with the androgen receptor (AR) and thyroid hormone receptors (TRs), making it a multi-target endocrine disruptor. It is also suspected of binding to transthyretin (TTR), disrupting thyroid hormone transport.
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| ln Vitro |
In vitro, 3-Chlorobisphenol A is a weak estrogen agonist. In a cell-based estrogen receptor (ER) transactivation assay using MCF-7 cells (E-SCREEN assay), 3-ClBPA (0.1-100 uM) induces cell proliferation (uterotrophic effect) and the expression of the estrogen-responsive pS2 gene. The EC₅0 for ER activation is in the low micromolar range, making it about 1000-fold less potent than 17beta-estradiol. It also acts as a weak antagonist of the androgen receptor (AR) in cell-based reporter assays. At concentrations of 10-100 uM, it inhibits dihydrotestosterone (DHT)-induced AR activation. It also induces the activity of CYP1A1 in HepG2 cells, as measured by the ethoxyresorufin-O-deethylase (EROD) assay. The compound is cytotoxic to MCF-7 cells at concentrations > 100 uM.
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| ln Vivo |
3-Chlorobisphenol A is not a drug; it is an environmental pollutant. In vivo, it has been shown to have estrogenic and anti-androgenic effects in animal models. In immature female rats, a single subcutaneous injection of 3-ClBPA (50-200 mg/kg) induces a dose-dependent increase in uterine weight, indicating estrogenic activity (uterotrophic assay). In male rats, exposure to 3-ClBPA (50-100 mg/kg/day, oral) for 14 days reduces serum testosterone levels and decreases the weight of the seminal vesicles and prostate. It also alters the expression of genes involved in steroidogenesis in the testes. The compound is used as a reference standard in ecotoxicology studies, not as a pharmacological tool.
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| Enzyme Assay |
The estrogenic activity of 3-Chlorobisphenol A is measured using a cell-based luciferase reporter gene assay. Human breast cancer MCF-7 cells are seeded in 96-well white plates (2×10⁴ cells/well) in phenol red-free medium with charcoal-stripped serum. After 24 h, the cells are transiently transfected with a plasmid containing an estrogen response element (ERE) and a luciferase reporter gene. The next day, the cells are treated with 3-ClBPA (0.1-100 uM) for 24 h. The positive control is 17beta-estradiol (0.01-100 nM). The cells are lysed, and luciferase activity is measured. The EC₅0 is calculated. The relative estrogenic potency is calculated as (EC₅0(17beta-estradiol) / EC₅0(3-ClBPA)). This bioassay is used to assess the estrogenic potency of chemicals.
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| Cell Assay |
For in vitro toxicity screening, HepG2 or MCF-7 cells are seeded in 96-well plates (1×10⁴ cells/well) and treated with 3-Chlorobisphenol A (1-1000 uM) for 24-72 h. Cell viability is measured by MTT assay. The CC₅0 is expected to be > 100 uM, indicating moderate cytotoxicity. For ERalpha binding, a competitive binding assay using purified ERalpha protein is performed. The receptor is incubated with a fluorescent ligand (e.g., Fluormone-ER) and varying concentrations of 3-ClBPA. The decrease in fluorescence polarization is measured. The IC₅0 for binding is calculated. For CYP1A1 induction, the EROD assay is used. HepG2 cells are treated with 3-ClBPA (1-50 uM) for 24 h. The cells are lysed, and ethoxyresorufin is added. The formation of the fluorescent product resorufin is measured. The EC₅0 for CYP1A1 induction is calculated.
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| Animal Protocol |
Uterotrophic assay in immature female rats: Female Sprague-Dawley rats (18-21 days old, 40-50 g, n=6/group) are injected subcutaneously with 3-Chlorobisphenol A (50, 100, or 200 mg/kg) in corn oil for 3 consecutive days. The positive control group receives 17beta-estradiol (0.5 ug/kg). The vehicle control group receives corn oil only. On day 4, the animals are euthanized, and the uteri are dissected, trimmed of fat, and weighed. The uterine weight (mg) is normalized to the body weight (g). An increase in the uterine weight/body weight ratio indicates estrogenic activity. The compound's potency is compared to that of 17beta-estradiol. The no-observed-effect level (NOEL) is determined. This protocol is for endocrine disruptor screening.
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| ADME/Pharmacokinetics |
3-Chlorobisphenol A is a lipophilic molecule (MW 262.73, LogP ~ 4.5). It is not a drug, and its PK is not studied therapeutically. Following oral exposure, it is rapidly absorbed from the gastrointestinal tract. It is distributed to the liver, adipose tissue, and uterus. It is metabolized by glucuronidation and sulfation, forming water-soluble conjugates that are excreted in the urine and bile. The elimination half-life in rodents is approximately 6-12 hours. For research use, it is stored as a solid at -20degC. It is soluble in DMSO, ethanol, and organic solvents. It is light sensitive. The compound is a reference standard for environmental monitoring.
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| Toxicity/Toxicokinetics |
For 3-Chlorobisphenol A, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). Signal word: Danger. Hazard statements: H360 (May damage fertility or the unborn child), H400 (Very toxic to aquatic life). Precautionary statements: P201 (Obtain special instructions before use), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). It is a potential endocrine disruptor and reproductive toxin. For research use only.
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| References | |
| Additional Infomation |
3-Chlorobisphenol A (3-ClBPA; CAS# 74192-35-1) is a research-grade chlorinated bisphenol A (BPA) standard. It is not an FDA-approved drug. It is used as a reference standard for the analysis of BPA derivatives in environmental samples, as a positive control in endocrine disruptor screening assays (ER, AR, AhR), and in studies of environmental toxicology. For research use only, not for diagnostic or therapeutic applications.
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| Molecular Formula |
C15H15CLO2
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| Molecular Weight |
262.73
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| Exact Mass |
262.076
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| CAS # |
74192-35-1
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| PubChem CID |
20161169
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| Appearance |
Typically exists as solids at room temperature
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| Hydrogen Bond Donor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
18
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| Complexity |
272
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)(C1=CC=C(C=C1)O)C2=CC(=C(C=C2)O)Cl
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| InChi Key |
XLRAFMYRFQJARM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H15ClO2/c1-15(2,10-3-6-12(17)7-4-10)11-5-8-14(18)13(16)9-11/h3-9,17-18H,1-2H3
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| Chemical Name |
2-chloro-4-[2-(4-hydroxyphenyl)propan-2-yl]phenol
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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 | 3.8062 mL | 19.0309 mL | 38.0619 mL | |
| 5 mM | 0.7612 mL | 3.8062 mL | 7.6124 mL | |
| 10 mM | 0.3806 mL | 1.9031 mL | 3.8062 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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