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Bisphenol B is a biochemical and analog of Bisphenol A, which is an endocrine disrupting chemical (EDC) and a substance of very high concern (SVHC) in the European Union (EU) for both human health. Bisphenol B shows endocrine disruptive properties or other adverse effects on animal models
| Animal Protocol |
Rat 28-Day Oral Study:** Male Sprague-Dawley rats (70-80 days old, n=7/group) were orally administered BPB at 0, 5, 25, 50 mg/kg BW/d for 28 days. Testis histology and hormone levels were assessed. [1]
* **Rat 48-Week Drinking Water Study:** Male Sprague-Dawley rats (PND 23, n=7/group) received BPB in drinking water at 0, 5, 25, 50 μg/L for 48 weeks. Water intake was monitored, and estimated daily intake calculated (0, 0.3, 1.5, 3 μg/kg/d). Reproductive organ weights, sperm parameters, testis histology, and hormone levels were assessed. [1] * **Zebrafish 21-Day Reproductive Study:** 4-month-old zebrafish (n=6/sex/group) were exposed to BPB at 0, 0.001, 0.01, 0.1, 1 mg/L in water for 21 days. Reproductive output (egg number), hatching rate, embryo survival, gonado-somatic index, hepato-somatic index, histology, hormone levels, and gene expression were assessed. [1] * **Uterotrophic Assay:** Immature female rats (PND 20, n=6-8/group) received subcutaneous injections of BPB at 200 mg/kg/d for 3 days. Uterine weight and morphology were assessed. [1] * **Hershberger Assay:** Castrated male rats received BPB (50-600 mg/kg/d) alone or with testosterone propionate for 10 days. Weights of androgen-dependent tissues were measured. [1] * **Medaka Study:** Male medaka were exposed to BPB at 0.5, 5, 50 μM for 8 hours. Hepatic gene expression was analyzed by qPCR. [1] |
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Researchers have previously demonstrated that bisphenol A [BPA; 2,2-bis(4-hydroxyphenyl)propane] or bisphenol B [BPB; 2,2-bis(4-hydroxyphenyl)butane] significantly enhances estrogenic activity upon incubation with rat liver S9 fraction. This metabolic activation requires the participation of microsomal and cytoplasmic components and has been observed not only in rat liver but also in human, monkey, and mouse liver S9 fractions. To identify the active metabolites of BPA and BPB, researchers analyzed the structures of the isolated active metabolites using negative ion mode liquid chromatography-tandem mass spectrometry (LC/MS/MS) and gas chromatography-mass spectrometry (GC/MS). The active metabolite of BPA showed a negative ion peak at [MH](-) 267 in LC/MS analysis and a single daughter ion peak at m/z 133 in MS/MS analysis, suggesting an isopropenylphenol dimer structure. Finally, multiple instrumental analyses confirmed that the active metabolite was identical to the standard 4-methyl-2,4-bis(p-hydroxyphenyl)pent-1-ene (MBP). The corresponding peaks of the BPB metabolite were [MH](-) 295 and m/z 147, indicating that it possesses an isobutylenylphenol dimer structure. Furthermore, co-incubation of BPA and BPB with rat liver S9 produced another active metabolite, which showed a negative ion peak at [MH](-) 281 and two daughter ion peaks at m/z 133 and m/z 147 in MS/MS analysis. These results strongly suggest that the active metabolites of BPA or BPB may be formed by the recombination of free radical fragments, which are single-electron oxidation products of carbon-phenyl bond cleavage. Notably, in multiple assays, the estrogenic activity of MBP, the active metabolite of BPA, was significantly stronger than that of maternal BPA, including two reporter gene assays using recombinant yeast expressing human estrogen receptor α and firefly luciferase plasmid transfected with MCF-7. |
| References |
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| Additional Infomation |
Bisphenol B is a type of bisphenol.
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| Molecular Formula |
C16H18O2
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|---|---|
| Molecular Weight |
242.3129
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| Exact Mass |
242.13
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| CAS # |
77-40-7
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| PubChem CID |
66166
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
412.2±25.0 °C at 760 mmHg
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| Melting Point |
126°C
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| Flash Point |
195.5±17.8 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.589
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| LogP |
3.96
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
18
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| Complexity |
226
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C1C([H])=C([H])C(=C([H])C=1[H])C(C([H])([H])[H])(C1C([H])=C([H])C(=C([H])C=1[H])O[H])C([H])([H])C([H])([H])[H]
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| InChi Key |
HTVITOHKHWFJKO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C16H18O2/c1-3-16(2,12-4-8-14(17)9-5-12)13-6-10-15(18)11-7-13/h4-11,17-18H,3H2,1-2H3
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| Chemical Name |
4-[2-(4-hydroxyphenyl)butan-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) |
DMSO : ~100 mg/mL (~412.69 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.32 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 (10.32 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (10.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.1269 mL | 20.6347 mL | 41.2694 mL | |
| 5 mM | 0.8254 mL | 4.1269 mL | 8.2539 mL | |
| 10 mM | 0.4127 mL | 2.0635 mL | 4.1269 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT04100421 | COMPLETED | Chronic Kidney Diseases Hemodialysis Complication | Shanghai Ninth People's Hospital Affiliated to Shanghai Jiao Tong University | 2017-06-01 | ||
| NCT04293900 | WITHDRAWN | Other: 24-hour dietary recall Other: Hand grip strength Other: International Physical Activity Questionnaire |
DLBCL Diffuse Large B Cell Lymphoma Non-Hodgkin Lymphoma |
George Washington University | 2021-01 |
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