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2-甲氧基雌三醇

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2-甲氧基雌三醇
IUPAC名
(8R,9S,13S,14S,16R,17R)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
别名 2-MeO-E3
识别
CAS号 1236-72-2  checkY
PubChem 102031
ChemSpider 92169
SMILES
 
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=CC(=C(C=C34)OC)O
InChI
 
  • 1S/C19H26O4/c1-19-6-5-11-12(14(19)9-16(21)18(19)22)4-3-10-7-15(20)17(23-2)8-13(10)11/h7-8,11-12,14,16,18,20-22H,3-6,9H2,1-2H3/t11-,12+,14-,16+,18-,19-/m0/s1
InChIKey PEXPJFWTSZLEAQ-YSYMNNNUSA-N
性质
化学式 C19H26O4
摩尔质量 318.41 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

2-甲氧基雌三醇(英语:2-Methoxyestriol,缩写2-MeO-E3)是一种内源性的雌激素代谢产物[1][2][3],主要是雌三醇2-羟基雌三醇的代谢产物[1][2][3]。2-MeO-E3对雌激素受体的亲和力极低,基本没有雌激素效应[4]。但是,2-MeO-E3有一些非雌激素受体介导的降血脂效应[5]

参考资料

  1. ^ 1.0 1.1 Fishman J, Gallagher TF. 2-Methoxyestriol: a new metabolite of estradiol in man. Arch. Biochem. Biophys. October 1958, 77 (2): 511–3. PMID 13584013. doi:10.1016/0003-9861(58)90097-3. 
  2. ^ 2.0 2.1 King RJ. Oestriol metabolism by rat- and rabbit-liver slices. Isolation of 2-methoxyoestriol and 2-hydroxyestriol. Biochem. J. May 1961, 79 (2): 355–61. PMC 1205847可免费查阅. PMID 13756104. doi:10.1042/bj0790355. 
  3. ^ 3.0 3.1 Fujii Y, Teranishi M, Nakada K, Yamazaki M, Kishida S, Miyabo S. Radioimmunoassay of 2-methoxyestriol in pregnancy plasma. Horm. Metab. Res. September 1988, 20 (9): 599–600. PMID 3198067. doi:10.1055/s-2007-1010895. 
  4. ^ Martucci CP. The role of 2-methoxyestrone in estrogen action. J. Steroid Biochem. July 1983, 19 (1B): 635–8. PMID 6310247. doi:10.1016/0022-4731(83)90229-7. 
  5. ^ Kono, Shinzo; Higa, Hiroaki; Sunagawa, Hajime. Hypocholesterolemic Effect of Long-Term Continuous Administration of 2-Methoxyestriol in Dietary Hypercholesterolemic Rats. Journal of Clinical Biochemistry and Nutrition. 1989, 6 (1): 49–56. ISSN 1880-5086. doi:10.3164/jcbn.6.49可免费查阅. 

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