17α-雌二醇
化合物
17α-雌二醇(英語:17α-Estradiol,缩写17α-E2)也称为17-表雌二醇(17-epiestradiol)或雌-1,3,5(10)-三烯-3,17α-二醇(estra-1,3,5(10)-triene-3,17α-diol)是一种较弱的内源性甾体雌激素,相对其C17上的差向异构体17β-雌二醇(通常就简称为雌二醇)仅在体内占少量[2][2]。17α-雌二醇的雌激素效价强度只有17β-雌二醇的百分之一[3],且更亲和雌激素受体中的ERα而非ERβ[2][4]。和上述核受体不同,对在大脑内表达的雌激素細胞表面受體ER-X而言,17α-雌二醇的亲和力比17β-雌二醇更高,说明17α-雌二醇是该受体的内源性配體[5]。
17α-雌二醇 | |
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IUPAC名 (8R,9S,13S,14S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol | |
别名 | 17α-E2; Alpha-Estradiol; Alfatradiol; 17-Epiestradiol; Estra-1,3,5(10)-triene-3,17α-diol; β-Estradiol (obsolete, misleading)[1] |
识别 | |
CAS号 | 57-91-0 |
PubChem | 68570 |
ChemSpider | 61840 |
SMILES |
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InChI |
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性质 | |
化学式 | C18H24O2 |
摩尔质量 | 272.38 g·mol−1 |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
参考文献
- ^ J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 897–. ISBN 978-1-4757-2085-3.
- ^ 2.0 2.1 2.2 Zhu BT, Han GZ, Shim JY, Wen Y, Jiang XR. Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor alpha and beta subtypes: Insights into the structural determinants favoring a differential subtype binding. Endocrinology. 2006, 147 (9): 4132–50. PMID 16728493. doi:10.1210/en.2006-0113.
- ^ Ralph M. Trüeb; Won-Soo Lee. Male Alopecia: Guide to Successful Management. Springer Science & Business Media. 13 February 2014: 93– [2019-03-16]. ISBN 978-3-319-03233-7. (原始内容存档于2020-01-31).
- ^ Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997, 138 (3): 863–70. PMID 9048584. doi:10.1210/endo.138.3.4979.
- ^ Toran-Allerand CD, Tinnikov AA, Singh RJ, Nethrapalli IS. 17alpha-estradiol: a brain-active estrogen?. Endocrinology. 2005, 146 (9): 3843–50. PMID 15947006. doi:10.1210/en.2004-1616.