17α-雌二醇

化合物

17α-雌二醇(英語:17α-Estradiol,縮寫17α-E2)也稱為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)是一種較弱的內源性甾體雌激素,相對其C17上的差向異構體17β-雌二醇(通常就簡稱為雌二醇)僅在體內佔少量[2][2]。17α-雌二醇的雌激素效價強度只有17β-雌二醇的百分之一[3],且更親和雌激素受體中的ERα而非ERβ[2][4]。和上述核受體不同,對在大腦內表達的雌激素細胞表面受體ER-X而言,17α-雌二醇的親和力比17β-雌二醇更高,說明17α-雌二醇是該受體的內源性配體[5]

17α-雌二醇
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
別名 17α-E2; Alpha-Estradiol; Alfatradiol; 17-Epiestradiol; Estra-1,3,5(10)-triene-3,17α-diol; β-Estradiol (obsolete, misleading)[1]
識別
CAS號 57-91-0
PubChem 68570
ChemSpider 61840
SMILES
 
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@H]2O)CCC4=C3C=CC(=C4)O
InChI
 
  • 1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1
性質
化學式 C18H24O2
摩爾質量 272.38 g·mol−1
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

參考文獻

  1. ^ 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. ^ 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. 
  3. ^ 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. (原始內容存檔於2020-01-31). 
  4. ^ 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. 
  5. ^ 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.