 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C18H22O3 |
| Molecular Weight | 286.36548 |
| Exact Mass | 286.157 |
| CAS # | 362-06-1 |
| Related CAS # | 2-Hydroxyestrone-d4;81586-97-2;2-Hydroxyestrone-13C6 |
| PubChem CID | 440623 |
| 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 |
| Index of Refraction | 1.609 |
| LogP | 3.523 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| 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 |
| 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) |
Biological Activity
| Targets | Human Endogenous Metabolite Estrogen receptor |
| 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]. |
| 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]. |
| 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. |
| 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. |
| ADME/Pharmacokinetics |
Metabolism / Metabolites 2-hydroxyestrone has known human metabolites that include Estrone 2-O-glucuronide, 2-Methoxyestrone, and 3-O-methoxyestrone. 2-hydroxyestrone is a known human metabolite of estrone. |
| References |
[1]. 2-Hydroxyestrone: the 'good' estrogen. J Endocrinol. 1996 Sep;150 Suppl:S259-65. [2]. Antiestrogen action of 2-Hydroxyestrone on MCF-7 human breast cancer cells. J Biol Chem. 1984 Apr 25;259(8):4840-5. [3]. Quantitation of catechol estrogens and their N-acetylcysteine conjugates in urine of rats and hamsters. Chem Res Toxicol. 2000 Dec;13(12):1208-13. |
| Additional Infomation |
2-hydroxyestrone is a 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2. It has a role as a human metabolite. It is a 2-hydroxy steroid and a member of catechols. It is functionally related to an estrone. 2-Hydroxyestrone has been reported in Homo sapiens with data available. 2-Hydroxyestrone is a metabolite formed during the catabolism of estrone by the liver through the hydroxylation of the carbon at position 2 by cytochrome P450 (CYP) enzymes, including CYP1A1 and 1A2, with potential anticarcinogenic activity. The mechanism of action for the antitumor activity of 2-hydroxyestrone is not known but this metabolic product has minimal estrogenic activity compared to the parent compound and other estrone metabolites. Additionally, O-methylation of this compound produces 2-methoxyestradiol (2-MeOE2), which is a potent inhibitor of both cell proliferation and angiogenesis. |
Solubility Data
| 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 |
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (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 |