エストロン
エストロン · グランズボリン · ホルモバリン · ケトヒドロキシエストリン · エストルゲノン · トコキン · ホリステリン · ヒエストロン
識別子と物理属性
| CAS No. | 53-16-7 |
|---|---|
| 分子式 | C18H22O2 |
| 平均分子量 | 270.4 g/mol |
| SMILES | CC12CCC3c4ccc(O)cc4CCC3C1CCC2=O |
| InChIKey | DNXHEGUUPJUMQT-CBZIJGRNSA-N |
| PubChem CID | 698 |
| ChEMBL | CHEMBL756 |
| ChEBI | CHEBI:95131 |
| 現地名 | エストロン |
化学・物理的性質
| XLogP | 3.1 |
|---|---|
| 極性表面積 | 37.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 20 |
| 形式電荷 | 0 |
| 複雑度 | 418 |
| 融点 | 258-260 °C(lit.) |
| 比旋光度 | 158 º (c=1, dioxane) |
| 沸点 | 353.48°C (rough estimate) |
| 密度 | 1.2360 |
| 屈折率 | 165 ° (C=1, Dioxane) |
| 引火点 | 9℃ |
| 貯蔵条件 | room temp |
| 溶解度 | クロロホルム（微量）、ジオキサン（微量）、エタノール（微量）、メタノール（微量）0.03g/L |
| 外観・状態 | 結晶性粉末または結晶 |
| pKa（酸解離定数） | pKa 10.77±0.02(H2O)(Approximate) |
| 色 | 白～ほぼ白 |
| Merck | 3708 |
| BRN | 1915077 |
| ヘンリー定数 | 2.6×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| 主な用途 | 医薬品医薬品低分子化合物 |
| 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 |
| CAS データベース | 53-16-7(CAS DataBase Reference) |
| NISTの化学物質情報 | 3-Hydroxyestra-1,3,5(10)-trien-17-one(53-16-7) |
| EPAの化学物質情報 | Estrone (53-16-7) |
化学的特性
Estrone is an odorless white crystalline powder.Estrone is supplied as a crystalline solid. A stock solution may be made by dissolving the estrone in an organic solvent purged with an inert gas. Estrone is soluble in organic solvents such as DMSO and dimethyl formamide (DMF). The solubility of estrone in these solvents is approximately 20 mg/ml.Estrone is sparingly soluble in aqueous buffers. For maximum solubility in aqueous buffers, estrone should first be dissolved in DMF and then diluted with the aqueous buffer of choice. Estrone has a solubility of approximately 0.15 mg/ml in a1:5 solution of DMF:PBS (pH 7.2) using this method. We do not recommend storing the aqueous solution for more than one day.
安全性と法規制
| 水環境危害等級（WGK） | 3 |
|---|---|
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | KG8575000 |
| 輸送番号（UN） | UN1230 - class 3 - PG 2 - Methanol, solution |
| 税関コード | 29335995 |
| 危険文句（R） | 45-60-61-64-40-63-39/23/24/25-23/24/25-11 |
| 化審法 | (9)-2145 |
| 危険表示 | T,F |
| 安全措置（S） | 53-45-36/37-16 |
| 環境リスク評価 | エストロン(53-16-7) |
| 危険等級 | Carc. 2Lact.Repr. 1A |
| 貯蔵分類 | 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects |
| 有害物質データ | 53-16-7(Hazardous Substances Data) |
用途
解説
エストロン，女性ホルモンの一種。動物の卵巣から分泌され発情作用を促す。妊婦の尿などから無色の結晶として抽出され、合成もでき、女性ホルモン欠乏症に用いる。精選版 日本国語大辞典 精選版
用途
薬理研究用。
用途
医薬(卵胞ホルモン)
説明
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.
使用
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.
一般的な説明
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.
製法・合成法
純化方法
Purify estrone by chromatography on silica gel, eluting with 2:1 hexane/EtOAc and recrystallising from EtOH or Et2O/EtOH. [Danishefsky & Cain J Am Chem Soc 98 4975 1976.] The acetate [901-93-9] crystallises from EtOH with m 125-127o. [Beilstein 8 III 1171.]