| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
Human Endogenous Metabolite Estrogen receptor
2-Hydroxyestrone is a metabolite of estrone with minimal estrogenic activity. It is often referred to as a "good" estrogen metabolite due to its potential anticarcinogenic properties. It is used as a research tool to study the balance between activating and deactivating pathways of estrogen metabolism and their impact on hormone-sensitive cancers. |
|---|---|
| ln Vitro |
2-Hydroxyestrone displays antiestrogen activity on MCF-7 human breast cancer cells. Addition of 2-Hydroxyestrone to the cell cultures in concentration of 1-1000 nM had no effect on cell growth and proliferation because of quick O-methylation of the catechol estrogen by catechol O-methyltransferase which is highly active in these cells. In the presence of quinalizarin, a powerful catechol O-methyltransferase inhibitor which inhibits the O-methylation of the steroid, 10 and 100 nM 2-Hydroxyestrone dramatically suppresses the development and proliferation of the cells[2].
2-Hydroxyestrone has minimal estrogenic activity compared to the parent compound and other estrone metabolites. It is a specific receptor-mediated antiestrogen with anticancer effects. Its mechanism of action for antitumor activity is not fully known, but it is a key part of the Phase I metabolism of estrogen via the C-2 hydroxylation pathway. |
| ln Vivo |
Rats treated with 2-Hydroxyestrone showed significantly different levels of both 2-OHE1 (2-OHE1; 2 mg/kg; administered ip.) and 2-OHE1 4-N-acetylcysteine thioether (2-OHE1 4SR) in the induced and noninduced groups[3].
2-Hydroxyestrone is a circulating biomarker of estrogen metabolism. In vivo, its ratio to 16alpha-hydroxyestrone (16alpha-OHE1) is studied as a potential risk marker for breast cancer. A higher ratio of 2-OHE1 to 16alpha-OHE1 is generally considered to be more protective, as the 16alpha-metabolite is more estrogenic. It is a key research tool for understanding individual susceptibility to estrogen-induced cancers. |
| Enzyme Assay |
Cell-free assays to study the formation of 2-Hydroxyestrone measure the activity of CYP1A1 and CYP1A2. Human liver microsomes or recombinant CYP enzymes are incubated with estrone substrate and NADPH. The reaction is stopped, and the concentration of 2-Hydroxyestrone produced is quantified by LC-MS/MS. The assay is used to study enzyme kinetics and the effects of various inhibitors or inducers.
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| Cell Assay |
Cell Proliferation Assay[2]
Cell Types: Human breast cancer cell lines MCF-7, MDA-MB-231, and MDA-MB-330 Tested Tested Concentrations: 1-1000 nM Incubation Duration: 6 days Experimental Results: 10 and 100 nM markedly suppressed the growth and proliferation of the cells in the presence of quinalizarin. The tumor cell growth-inhibitory action of the catechol estrogen was neutralized by the presence of 1 nM estradiol. Estrogen metabolism studies are conducted using primary human hepatocytes or HepG2 cells. Cells are treated with estradiol or estrone for 24-72 hours. The culture medium is collected, and the levels of 2-Hydroxyestrone and other metabolites (e.g., 16alpha-OHE1) are quantified using a validated LC-MS/MS method to assess the metabolic phenotype and the ratio of "good" to "bad" estrogen metabolites. |
| Animal Protocol |
Animal/Disease Models: Female and male SD (Sprague-Dawley) rats (6 weeks old)[3]
Doses: 2 mg/kg Route of Administration: Administered ip Experimental Results: Levels of both 2-OHE1 and 2-OHE1 4SR in rats treated with 2-OHE1 were Dramatically different between the induced and noninduced groups. In vivo studies for 2-Hydroxyestrone are typically observational, measuring its levels in animal models of cancer. Rodents are administered estradiol or placed on specific diets to study how genetic or environmental factors alter estrogen metabolism. Blood, urine, and tissue samples are collected to quantify 2-Hydroxyestrone levels and correlate them with cancer risk biomarkers. |
| ADME/Pharmacokinetics |
Metabolism / Metabolites
Known metabolites of 2-hydroxyestrone include estrone 2-O-glucuronide, 2-methoxyestrone, and 3-O-methoxyestrone. 2-Hydroxyestrone is a known metabolite of estrone. 2-Hydroxyestrone is an endogenous metabolite, so its pharmacokinetics are linked to the parent hormone, estradiol. It is formed primarily in the liver and circulates bound to sex hormone-binding globulin (SHBG). It is rapidly conjugated by glucuronidation or sulfation and excreted in the urine, serving as an endpoint for metabolic studies. |
| Toxicity/Toxicokinetics |
2-Hydroxyestrone itself has low toxicity, as it is a natural, protective metabolite. Research suggests it is not directly harmful and may have chemopreventive properties. Its primary use in toxicology is as a biomarker to determine whether an environmental chemical or drug is altering estrogen metabolism toward a more carcinogenic profile (i.e., increased 16alpha-hydroxylation).
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| References | |
| Additional Infomation |
2-Hydroxyestrone is a 2-hydroxy steroid, a product of estrone with a hydroxyl group replaced at the 2-position. It is a human metabolite belonging to the catechol group and functionally related to estrone. 2-Hydroxyestrone has been reported to exist in humans, with supporting data. It is a metabolite formed during the liver metabolism of estrone, produced through hydroxylation of the 2-carbon of estrone by cytochrome P450 (CYP) enzymes (including CYP1A1 and 1A2), and possesses potential anticancer activity. The mechanism of its antitumor activity is not yet fully understood, but compared to the parent compound and other estrone metabolites, this metabolite exhibits extremely low estrogenic activity. Furthermore, O-methylation of this compound yields 2-methoxyestradiol (2-MeOE2), a potent inhibitor of cell proliferation and angiogenesis.
2-Hydroxyestrone is a naturally occurring catechol estrogen metabolite. It is a key research compound in the fields of cancer prevention and endocrinology, used as a standard for biomarker studies and to explore the role of the 2-hydroxylation pathway in hormone-dependent diseases. It is an analytical standard for research use. |
| Molecular Formula |
C18H22O3
|
|---|---|
| Molecular Weight |
286.36548
|
| Exact Mass |
286.157
|
| CAS # |
362-06-1
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| Related CAS # |
2-Hydroxyestrone-d4;81586-97-2;2-Hydroxyestrone-13C6
|
| PubChem CID |
440623
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| Appearance |
White to light yellow solid powder
|
| Density |
1.241g/cm3
|
| Boiling Point |
481.3ºC at 760 mmHg
|
| Melting Point |
199-201ºC
|
| Flash Point |
259ºC
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| Index of Refraction |
1.609
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| LogP |
3.523
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| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
0
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| Heavy Atom Count |
21
|
| Complexity |
448
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
OC1=C(O)C=C2[C@H]3CC[C@@]4(C(CC[C@H]4[C@@H]3CCC2=C1)=O)C
|
| InChi Key |
SWINWPBPEKHUOD-JPVZDGGYSA-N
|
| InChi Code |
InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1
|
| Chemical Name |
(8R,9S,13S,14S)-2,3-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
|
| 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 | 3.4920 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.
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