エストラジオール

解説エストラジオール，白色の結晶または結晶性粉末．融点173～179 ℃．[α]D20"＋76～＋83°(ジオキサン)．水にほとんど難溶，ジオキサンに可溶．アセトンにやや易溶，エタノールにやや難溶，ごま油に難溶．代表的な発情ホルモンであり，プロゲステロンとともに子宮内膜を増殖させて周期的な変化を誘発し，妊卵の着床，妊娠の成立に重要な役割を果たしている．無月経，不妊症，更年期障害などの治療に用いられる．エストラジオールのエステル誘導体には17-ベンゾイルエストラジオール3-ベンゾエートなどが知られている．森北出版「化学辞典（第2版）

用途生体内代謝経路の研究、種々の癌に及ぼす性ホルモンの影響などの研究用。

用途卵胞ホルモン剤です。

用途卵胞ホルモン剤です。

使用17β-Estradiol is the major estrogen secreted by the premenopausal ovary.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Estradiol, estra-1,3,5(10)-triene-3,17β-diol, is the most activeof the natural steroid estrogens. Although its 17β-OHgroup is vulnerable to bacterial and enzymatic oxidation toestrone, it can be temporarily protected as anester at C3 or C17, or permanently protected by adding a17α-alkyl group (e.g., 17α-ethinyl estradiol, the most commonlyused estrogen in oral contraceptives). The increasedoil solubility of the 17β-esters (relative to estradiol) permitsthe esters to remain in oil at the IM injection site for extendedperiods. These derivatives illustrate the principles of steroidmodification. Transdermal estradiolproducts avoid first-pass metabolism, allowing estradiol tobe as effective as oral estrogens for treating menopausalsymptoms. A new transdermal spray, Evamist, was approvedin 2007. Estradiol itself is typically not very effective orallybecause of rapid metabolism, but an oral formulation of micronizedestradiol that allows more rapid absorption of thedrug is available (Estrace). In addition to the oral and transdermalproducts, estradiol is also available in gel, cream, andvaginal ring formulations. The commercially available estradiolesters are the following:Estradiol 3-acetate, USP (oral; vaginal ring)Estradiol 17-valerate, USP (IM injection)Estradiol 17-cypionate, USP (IM injection).

純化方法17-Estradiol (previously known as -estradiol) is purified by chromatography on SiO2 (toluene/EtOAc 4:1) and recrystallised from CHCl3/hexane or 80% EtOH. It is stable in air, is insoluble in H2O, and is precipitated by digitonin. The UV has max at 225 and 280 nm. The diacetate [3434-88-6] has m 97-98o and forms leaflets from aqueous EtOH. The 3-benzoate crystallises from aqueous MeOH withm 193o and [] D 25 +58o to 63o (c 1, dioxane). [Meischer & Scholz Helv Chim Acta 20 263, 1237 1937, Biochem J 32 1273 1938, Oppolzer & Roberts Helv Chim Acta 63 1703 1980, Inhoffen & Zühlsdorff Chem Ber 7 4 1914 1941, Beilstein 6 IV 6611.]