| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
Target: Isotope-Labeled Compounds / Environmental Metabolite. 4-Hydroxybenzophenone is a UV absorber and an endocrine-disrupting chemical (EDC) with weak estrogenic and anti-androgenic activity. It is a metabolite of benzophenone-3 (oxybenzone), a common sunscreen ingredient. The labeled version is an analytical standard for environmental and biomonitoring studies, with no biological activity as a labeled compound.
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|---|---|
| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
In vitro, the labeled standard has no direct biological activity. The unlabeled 4-hydroxybenzophenone (1-100 uM) exhibits weak estrogenic activity (EC50 ~1-10 uM) in E-screen assays with MCF-7 breast cancer cells and binds to estrogen receptors (ERalpha and ERbeta) with Ki values in the micromolar range. It also shows anti-androgenic activity by antagonizing androgen receptor (AR)-mediated transcription at higher concentrations (IC50 ~10-50 uM). The labeled standard is used for analytical method development. |
| ln Vivo |
In vivo, the unlabeled 4-hydroxybenzophenone is a major metabolite of benzophenone-3 excreted in human urine after sunscreen application or dietary exposure. It has been detected in environmental samples (water, soil, biota) and in human breast milk, plasma, and urine, serving as a biomarker of benzophenone exposure. The deuterated standard is used to accurately quantify this metabolite in biomonitoring and environmental studies.
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| Enzyme Assay |
For cell-free assays (LC-MS/MS): urine, plasma, or water samples are spiked with 4-Hydroxybenzophenone-d4 internal standard. After enzymatic hydrolysis (to deconjugate glucuronides/sulfates) and solid-phase extraction (SPE) or liquid-liquid extraction, the samples are analyzed by LC-MS/MS equipped with a C18 column. Quantitation of 4-hydroxybenzophenone is based on the analyte/internal standard peak area ratio using isotope dilution mass spectrometry. The deuterated standard corrects for matrix effects and extraction recovery.
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| Cell Assay |
No cell-based assays are performed with the labeled standard. The unlabeled 4-hydroxybenzophenone is tested in E-screen proliferation assays using MCF-7 cells. Cells are treated with the compound (0.01-100 uM, 6 days), and cell proliferation is measured by sulforhodamine B (SRB) or MTT assay. Estrogenic activity is compared to estradiol (positive control). The labeled standard is not used in these assays.
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| Animal Protocol |
No animal studies are conducted with the labeled internal standard itself. For biomonitoring studies, animals (rats, mice) exposed to benzophenone-3 or related UV filters have urine, plasma, or tissue samples collected. The labeled internal standard is used in LC-MS/MS bioanalysis to quantify 4-hydroxybenzophenone concentrations as a biomarker of exposure. Toxicokinetic studies of benzophenone-3 use the labeled standard to measure metabolite levels.
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| ADME/Pharmacokinetics |
PK properties of 4-hydroxybenzophenone: after dermal or oral exposure to benzophenone-3, it is rapidly absorbed and extensively metabolized to 4-hydroxybenzophenone by CYP450 enzymes (primarily CYP2C19 and CYP3A4). The metabolite is then conjugated with glucuronic acid or sulfate and excreted in urine. Plasma half-life of 4-hydroxybenzophenone is approximately 2-4 h in rodents. The deuterated standard co-elutes with the analyte, ensuring accurate quantitation by stable isotope dilution mass spectrometry.
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| Toxicity/Toxicokinetics |
Toxicity profile: 4-Hydroxybenzophenone is considered an endocrine-disrupting chemical (EDC). In animal studies, it has been shown to have weak estrogenic and anti-androgenic effects at high doses (≥100 mg/kg/day). It may also cause skin sensitization in susceptible individuals. No acute toxicity is observed at typical environmental exposure levels. The labeled standard is for research use only and is non-hazardous for transport under normal laboratory conditions. Not for human consumption.
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| References | |
| Additional Infomation |
4-Hydroxybenzophenone-d4 is a research standard, not a drug. It is not FDA-approved for clinical use. It is used as an internal standard for environmental monitoring (water, soil, sediment), food safety testing (food packaging materials), and biomonitoring studies of UV filter exposure in human populations (e.g., assessment of sunscreen safety and environmental impact). The labeled compound is essential for compliance with regulatory guidelines (e.g., EU Cosmetics Regulation, FDA sunscreen monographs) for quantification of benzophenone metabolites. It is also used in quality control for personal care products and pharmaceuticals containing benzophenone UV absorbers.
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| Molecular Formula |
C13H10O2
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|---|---|
| Molecular Weight |
198.217303752899
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| Exact Mass |
202.093
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| CAS # |
93496-64-1
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| PubChem CID |
12299668
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
3.1
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
15
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| Complexity |
211
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[2H]C1=C(C(=C(C(=C1C(=O)C2=CC=CC=C2)[2H])[2H])O)[2H]
|
| InChi Key |
NPFYZDNDJHZQKY-YKVCKAMESA-N
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| InChi Code |
InChI=1S/C13H10O2/c14-12-8-6-11(7-9-12)13(15)10-4-2-1-3-5-10/h1-9,14H/i6D,7D,8D,9D
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| Chemical Name |
phenyl-(2,3,5,6-tetradeuterio-4-hydroxyphenyl)methanone
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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 | 5.0449 mL | 25.2245 mL | 50.4490 mL | |
| 5 mM | 1.0090 mL | 5.0449 mL | 10.0898 mL | |
| 10 mM | 0.5045 mL | 2.5224 mL | 5.0449 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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