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IUPAC name
Other names
4-ME2; 4-MeOE2; 4-MeO-E2; 4-Methoxy-17β-estradiol; 4-Methoxyestra-1,3,5(10)-triene-17β-diol; Estra-1,3,5(10)-trien-3,4,17β-triol 4-methyl ether
  • 26788-23-8
3D model (JSmol)
  • Interactive image
  • CHEBI:136975
  • 61848
PubChem CID
  • 68578
Molar mass 302.414 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

4-Methoxyestradiol (4-ME2) is an endogenous, naturally occurring methoxylated catechol estrogen and metabolite of estradiol that is formed by catechol O-methyltransferase via the intermediate 4-hydroxyestradiol.[1][2][3] It has estrogenic activity similarly to estrone and 4-hydroxyestrone.[4]

Relative affinities and uterotrophic efficacies of estrogens

Estrogen ER RBA (%) Uterine weight (%)
Control 100
Estradiol 100 506
Estriol 10 468
2-Hydroxyestradiol 24 285
2-Methoxyestradiol 0.05 101
4-Hydroxyestradiol 45 ?
4-Methoxyestradiol 13 260
2-Hydroxyestrone 2 130
2-Methoxyestrone 0.01 ?
4-Hydroxyestrone 11 351
4-Methoxyestrone 0.13 338
Notes: ER (rat uterine cytosol) RBA + estrogenicity (change in rat uterine wet weight) of estrogen metabolites. Sources: See template.

See also


  1. ^ http://www.hmdb.ca/metabolites/HMDB12782
  2. ^ Anna R. Hemnes (16 December 2015). Gender, Sex Hormones and Respiratory Disease: A Comprehensive Guide. Humana Press. pp. 32–. ISBN 978-3-319-23998-9.
  3. ^ Christian Lauritzen; John W. W. Studd (22 June 2005). Current Management of the Menopause. CRC Press. pp. 378–379. ISBN 978-0-203-48612-2.
  4. ^ Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK (2000). "Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women". J. Soc. Gynecol. Investig. 7 (3): 175–83. doi:10.1016/s1071-5576(00)00049-6. PMID 10865186.

External links

  • Metabocard for 4-Methoxyestradiol - Human Metabolome Database

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