Ketohydroxy-Estratriene
Estron · OESTRONE · 200-164-5 · Esterone · Hiestrone · 1,3,5(10)-ESTRATRIEN-3-OL-17-ONE · ESTROL · (8R,9S,13S,14S)-3-hydroxy-13-Methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one
Identifiers & Physical Properties
| CAS No. | 53-16-7 |
|---|---|
| Molecular formula | C18H22O2 |
| Average molar mass | 270.4 g/mol |
| SMILES | CC12CCC3c4ccc(O)cc4CCC3C1CCC2=O |
| InChIKey | DNXHEGUUPJUMQT-CBZIJGRNSA-N |
| PubChem CID | 698 |
| ChEMBL | CHEMBL756 |
| ChEBI | CHEBI:95131 |
Chemical & Physical Properties
| XLogP | 3.1 |
|---|---|
| Topological polar surface area | 37.3 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 20 |
| Formal charge | 0 |
| Complexity | 418 |
| Melting point | 258-260 °C(lit.) |
| alpha | 158 º (c=1, dioxane) |
| Boiling point | 353.48°C (rough estimate) |
| Density | 1.2360 |
| Refractive index | 165 ° (C=1, Dioxane) |
| Flash point | 9℃ |
| Storage conditions | room temp |
| Solubility | Chloroform (Slightly), Dioxane (Slightly), Ethanol (Slightly), Methanol (Slightly)0.03 g/L |
| Physical state | Crystalline Powder or Crystals |
| pKa (acidity coefficient) | pKa 10.77±0.02(H2O)(Approximate) |
| Color | White to almost white |
| Merck | 3708 |
| BRN | 1915077 |
| Henry's law constant | 2.6×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| Major applications | pharmaceuticalpharmaceutical small molecule |
| InChI | 1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1 |
| InChIKey | DNXHEGUUPJUMQT-CBZIJGRNSA-N |
| SMILES | C[C@]12CC[C@H]3[C@@H](CCc4cc(O)ccc34)[C@@H]1CCC2=O |
| FDA 21 CFR | 310.545 |
| CAS DataBase Reference | 53-16-7(CAS DataBase Reference) |
| EWG's Food Scores | 3-6 |
| FDA UNII | 2DI9HA706A |
| Proposition 65 List | Estrone |
| ATC code | G03CA07,G03CC04 |
| NIST Chemistry Reference | 3-Hydroxyestra-1,3,5(10)-trien-17-one(53-16-7) |
| EPA Substance Registry System | Estrone (53-16-7) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS08 |
| Signal word | Danger |
| GHS hazard statements | H351-H360FD-H362 |
| GHS precautionary statements | P202-P260-P263-P264-P270-P308+P313 |
| Hazard symbols | T,F |
| Risk statements (R) | 45-60-61-64-40-63-39/23/24/25-23/24/25-11 |
| Safety statements (S) | 53-45-36/37-16 |
| UN transport number | UN1230 - class 3 - PG 2 - Methanol, solution |
| Water hazard class (WGK) | 3 |
| RTECS number | KG8575000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29335995 |
| Storage class | 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects |
| Hazard class | Carc. 2Lact.Repr. 1A |
| Hazardous substances data | 53-16-7(Hazardous Substances Data) |
| REACH registrations | Active |
Safety & Regulations
| Water hazard class (WGK) | 3 |
|---|---|
| TSCA inventory status | TSCA listed |
| RTECS number | KG8575000 |
| UN transport number | UN1230 - class 3 - PG 2 - Methanol, solution |
| Customs code | 29335995 |
| Risk statements (R) | 45-60-61-64-40-63-39/23/24/25-23/24/25-11 |
| Signal word | Danger |
| GHS pictogram | GHS08 |
| Hazard symbols | T,F |
| Safety statements (S) | 53-45-36/37-16 |
| Storage class | 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects |
| GHS hazard statements | H351-H360FD-H362 |
| REACH registrations | Active |
| Hazard class | Carc. 2Lact.Repr. 1A |
| GHS precautionary statements | P202-P260-P263-P264-P270-P308+P313 |
| Hazardous substances data | 53-16-7(Hazardous Substances Data) |
Applications & Uses
Description
Estrone is one of the three naturally occurring estrogens, the others being estradiol and estriol. Estrone is synthesized from androstenedione by the aromatase enzyme system in the ovaries and placenta, and is also synthesized from estradiol by 17-hydroxy steroid dehydrogenase in the liver.Serum concentrations of estrone in premenopausal women fluctuate according to the menstrual cycle and becomes the most predominant estrogen in postmenopausal women.The binding affinities of estrone to the estrogen receptors α and β are approximately 60% and 37% relative to estradiol.
Uses
Estrone is a metabolite of 17β-Estradiol (E888000). During the metabolism, it is in rapid equilibrium with Estriol (E888960) and 17β-Estradiol (E888000) (1). Causes the feminization of male fish at human and animal waste sites (2). This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.
Uses
A metabolite of 17β-Estradiol.
Uses
Estrone is a weak form of estrogen and exists as estrone sulphate. Estrone is a luteolytic estrogen produced by the corpus luteum. In the follicle, estrone is synthesized from androstenedione by the action of cytochrome P450 aromatase.Estrone has been used:as medium supplement for hormone based degranulation studies of natural killer cells.as an endocrine disrupting compound for screening bacterial biosensor in toxic water.as medium component for monitoring fatty acid synthase (FASN) activity in breast adenocarcinoma cell lines.
General Description
Estrone, 3-hydroxyestra-1,3,5(10)-trien-17-one, is less active than estradiol but more active than itsmetabolite, estriol. As the salt of its 3-sulfate ester, estroneis the primary ingredient in conjugated estrogens, USP, andesterified estrogens, USP. Although originally obtainedfrom the urine of pregnant mares (about 10 mg/L), estroneis now prepared synthetically. Estrone itself is not availablein commercial oral formulations, but can be obtained at compounding pharmacies as a topical formulation. Oleoylestrone,the C3 ester of estrone with oleic acid, is in phase IIclinical trials for the treatment of obesity. This acyl estronederivative reduces fat stores by a mechanism not involvingthe ER, although some of the oleoyl-estrone is hydrolyzedto estrone in vivo.