4-Methoxyestriol

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4-Methoxyestriol
4-methoxyestriol.svg
Names
Preferred IUPAC name
(1R,2R,3aS,3bR,9bS,11aS)-6-Methoxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,7-triol
Other names
4-MeO-E3; 4-Methoxyestra-1,3,5(10)-triene-3,16α,17β-triol
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C19H26O4/c1-19-8-7-11-10-5-6-15(20)17(23-2)13(10)4-3-12(11)14(19)9-16(21)18(19)22/h5-6,11-12,14,16,18,20-22H,3-4,7-9H2,1-2H3/t11-,12-,14+,16-,18+,19+/m1/s1
    Key: MTZUPVFOGAXGJG-JUVWIQMMSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4OC)O
Properties
C19H26O4
Molar mass 318.413 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Methoxyestriol (4-MeO-E3) is an endogenous estrogen metabolite.[1][2][3][4] It is the 4-methyl ether of 4-hydroxyestriol and a metabolite of estriol and 4-hydroxyestriol.[1][2][3] 4-Methoxyestriol has very low affinities for the estrogen receptors.[4] Its relative binding affinities (RBAs) for estrogen receptor alpha (ERα) and estrogen receptor beta (ERβ) are both about 1% of those of estradiol.[4] For comparison, estriol had RBAs of 11% and 35%, respectively.[4]

See also[edit]

References[edit]

  1. ^ a b Gerhardt K, Ludwig-Köhn H, Henning HV, Remberg G, Zeeck A (February 1989). "Identification of oestrogen metabolites in human urine by capillary gas chromatography and mass spectrometry". Biomed. Environ. Mass Spectrom. 18 (2): 87–95. doi:10.1002/bms.1200180202. PMID 2706375.
  2. ^ a b Gaikwad NW (May 2013). "Ultra performance liquid chromatography-tandem mass spectrometry method for profiling of steroid metabolome in human tissue". Anal. Chem. 85 (10): 4951–60. doi:10.1021/ac400016e. PMID 23597399.
  3. ^ a b Fujii Y, Teranishi M, Nakada K, Yamazaki M, Kishida S, Miyabo S (February 1992). "Radioimmunoassay for the determination of 2-methoxyestriol concentration in plasma of pregnant women". Chem. Pharm. Bull. 40 (2): 410–3. doi:10.1248/cpb.40.410. PMID 1606638.
  4. ^ a b c d Zhu BT, Han GZ, Shim JY, Wen Y, Jiang XR (September 2006). "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. 147 (9): 4132–50. doi:10.1210/en.2006-0113. PMID 16728493.