에스트론
에스트론 · Estron · OESTRONE · 200-164-5 · Esterone · Hiestrone · 1,3,5(10)-ESTRATRIEN-3-OL-17-ONE · ESTROL
식별자 및 물리적 특성
| CAS No. | 53-16-7 |
|---|---|
| 분자식 | C18H22O2 |
| 평균 분자량 | 270.4 g/mol |
| SMILES | CC12CCC3c4ccc(O)cc4CCC3C1CCC2=O |
| InChIKey | DNXHEGUUPJUMQT-CBZIJGRNSA-N |
| PubChem CID | 698 |
| ChEMBL | CHEMBL756 |
| ChEBI | CHEBI:95131 |
| 현지명 | 에스트론 |
화학 및 물리적 성질
| XLogP | 3.1 |
|---|---|
| 극성 표면적 | 37.3 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 20 |
| 형식 전하 | 0 |
| 복잡도 | 418 |
| 녹는점 | 258-260 °C(lit.) |
| 끓는 점 | 353.48°C (rough estimate) |
| 밀도 | 1.2360 |
| 굴절률 | 165 ° (C=1, Dioxane) |
| 인화점 | 9℃ |
| 저장 조건 | room temp |
| 용해도 | 클로로포름(약간 용해됨), 디옥산(약간 용해됨), 에탄올(약간 용해됨), 메탄올(약간 용해됨) |
| 물리적 상태 | 결정질 분말 또는 결정 |
| pKa(산도 계수) | pKa 10.77±0.02(H2O)(Approximate) |
| 색상 | 흰색에서 거의 흰색 |
| 용해도 | 0.03g/L |
| Merck | 3708 |
| BRN | 1915077 |
| 헨리 상수 | 2.6×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| 주요 응용 | 제약소분자 약용 |
| 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 |
| NIST | 3-Hydroxyestra-1,3,5(10)-trien-17-one(53-16-7) |
| EPA | Estrone (53-16-7) |
화학적 성질
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.
안전 및 규제
| 수질 위해 등급(WGK) | 3 |
|---|---|
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | KG8575000 |
| 운송 번호(UN) | UN1230 - class 3 - PG 2 - Methanol, solution |
| 관세 코드 | 29335995 |
| 위험 문구(R) | 45-60-61-64-40-63-39/23/24/25-23/24/25-11 |
| 위험 표시 | T,F |
| 안전 문구(S) | 53-45-36/37-16 |
| 위험 등급 | Carc. 2Lact.Repr. 1A |
| 저장 분류 | 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects |
| 유해 물질 데이터 | 53-16-7(Hazardous Substances Data) |
용도
개요
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.
용도
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.
일반 설명
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.