| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| 5mg |
|
||
| 10mg |
|
||
| Other Sizes |
| Targets |
Human Endogenous Metabolite
16alpha-Hydroxyestrone targets the estrogen receptor (ERalpha and ERbeta), similar to other estrogens. It binds to estrogen receptors with lower affinity than estradiol but with greater potency than 2-hydroxyestrone. 16alpha-Hydroxyestrone has been reported to exhibit estrogenic activity and can covalently bind to estrogen receptors via its reactive keto group. It may also influence other hormone-sensitive pathways. |
|---|---|
| ln Vitro |
Elevated levels of 16α-hydroxyestrone and E3, which are active metabolites of estrogen, have been linked to higher bone mineral density [1].
In vitro, 16alpha-Hydroxyestrone exhibits estrogenic activity and can stimulate the proliferation of estrogen-dependent breast cancer cell lines such as MCF-7. It has been shown to induce anchorage-independent growth in soft agar assays, suggesting potential genotoxic or proliferative effects. The compound also forms covalent adducts with DNA in cell-free systems and in cultured cells, raising concerns about its potential role in estrogen-induced carcinogenesis. |
| ln Vivo |
In vivo, 16alpha-Hydroxyestrone is a major urinary metabolite of estrone and estradiol. Elevated levels of 16alpha-hydroxyestrone relative to 2-hydroxyestrone (the 16alpha/2-OH estrone ratio) have been associated with increased risk of breast cancer in some epidemiological studies. The compound has been proposed as a potential biomarker for estrogen metabolism and breast cancer risk, although findings have been inconsistent across studies.
|
| Enzyme Assay |
16alpha-Hydroxyestrone can be used in non-cellular enzyme assays. For enzyme activity studies, the compound is dissolved in DMSO or ethanol to prepare a stock solution. It is then used as a substrate or standard in CYP450 enzyme assays to study 16alpha-hydroxylation of estrone. For estrogen receptor binding assays, the compound is diluted into assay buffer (e.g., 50 mM Tris-HCl, pH 7.4, containing 0.1% BSA) and tested for competitive binding to estrogen receptors using [3H]estradiol as a radioligand.
|
| Cell Assay |
For in vitro cellular experiments, estrogen-dependent MCF-7 cells are cultured in phenol red-free RPMI-1640 medium with charcoal-stripped FBS. Cells are treated with 16alpha-Hydroxyestrone at concentrations ranging from 0.1 nM to 1 uM for 24-72 hours. Cell proliferation is measured by MTT assay or by counting cell numbers. Estrogen-responsive gene expression (e.g., pS2, progesterone receptor) is measured by qPCR. DNA adduct formation can be assessed by 32P-postlabeling.
|
| Animal Protocol |
For in vivo animal experiments, 16alpha-Hydroxyestrone is typically administered to ovariectomized female rats via subcutaneous injection (e.g., 1-100 ug/kg/day) or via osmotic minipump for continuous delivery. Uterine weight gain is measured as a marker of estrogenicity. Blood and urine samples are collected for LC-MS analysis of estrogen metabolites. Mammary tissue may be collected for histological analysis in carcinogenesis studies.
|
| ADME/Pharmacokinetics |
16alpha-Hydroxyestrone has a short half-life in plasma (∼30-60 minutes) due to rapid conjugation (glucuronidation, sulfation) and further metabolism to estriol. The compound is primarily eliminated in urine as conjugates. The metabolic ratio of 16alpha-hydroxyestrone to 2-hydroxyestrone in urine is influenced by genetic polymorphisms in CYP enzymes (CYP3A4, CYP1A1) and dietary factors such as indole-3-carbinol from cruciferous vegetables.
|
| Toxicity/Toxicokinetics |
16alpha-Hydroxyestrone is an endogenous estrogen metabolite and is not considered acutely toxic at physiological levels. However, epidemiological evidence suggests that a higher 16alpha/2-hydroxyestrone ratio may be associated with increased breast cancer risk. The compound has been shown to form covalent adducts with DNA in vitro, raising concerns about potential genotoxicity. In research, standard precautions for handling estrogenic compounds should be observed.
|
| References | |
| Additional Infomation |
16α-Hydroxyestrone is a 16α-hydroxy derivative of estrone and a minor estrogen metabolite. It is a metabolite found in mice, human serum, estrogen, and human urine. It is a 16α-hydroxy steroid, a secondary α-hydroxy ketone, a 3-hydroxy steroid, and a 17-oxo steroid. Its function is related to estrone. There are reports of the presence of 16α-hydroxyestrone in humans, with relevant data. 16α-Hydroxyestrone is a metabolite formed during the catabolism of estrone in the liver. Its formation is achieved through the hydroxylation of the 16-carbon of estrone by cytochrome P450 (CYP) family enzymes (including CYP3A4 and 3A5), and it possesses potential carcinogenic activity. Compared to the parent compound, 16α-hydroxyestrone (16α-OHE1) exhibits enhanced estrogenic activity, increasing the expression of estrogen receptor (ER) response genes, thereby leading to increased proliferation of susceptible tumor cells. The ratio between two estrogen metabolites—the weak estrogen 2-hydroxyestrone (2-OHE1) (a metabolite of the 2-hydroxylation pathway) and 16α-OHE1 (a metabolite of the 16-hydroxylation pathway)—can be used to assess the risk of certain cancers; a higher 2-OHE1:16α-OHE1 ratio is associated with a lower cancer risk.
See also: 16-hydroxyestrone (note moved to). 16alpha-Hydroxyestrone is not a drug but an endogenous estrogen metabolite and research compound. It has no approved therapeutic status. It is used as a biomarker in clinical research to assess estrogen metabolism patterns and breast cancer risk. The compound is also used in research on estrogen carcinogenesis, hormone-dependent cancers, and endocrine disruptor screening. 16alpha-Hydroxyestrone is available as an analytical standard for LC-MS/MS methods in clinical diagnostics and metabolomics studies. |
| Molecular Formula |
C18H22O3
|
|---|---|
| Molecular Weight |
286.37
|
| Exact Mass |
286.156
|
| CAS # |
566-76-7
|
| PubChem CID |
115116
|
| Appearance |
White to off-white solid powder
|
| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
493.2±45.0 °C at 760 mmHg
|
| Melting Point |
209-211ºC
|
| Flash Point |
266.2±25.2 °C
|
| Vapour Pressure |
0.0±1.3 mmHg at 25°C
|
| Index of Refraction |
1.612
|
| LogP |
2.32
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
21
|
| Complexity |
448
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H](C2=O)O)CCC4=C3C=CC(=C4)O
|
| InChi Key |
WPOCIZJTELRQMF-QFXBJFAPSA-N
|
| InChi Code |
InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
|
| Chemical Name |
(8R,9S,13S,14S,16R)-3,16-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-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 (In Vitro) |
DMSO: ≥ 250 mg/mL (873.00 mM)
|
|---|---|
| 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 | 3.4920 mL | 17.4599 mL | 34.9199 mL | |
| 5 mM | 0.6984 mL | 3.4920 mL | 6.9840 mL | |
| 10 mM | 0.3492 mL | 1.7460 mL | 3.4920 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
