16β,17α-Epiestriol

16β,17α-Epiestriol, or 16,17-epiestriol, also known as 16β-hydroxy-17α-estradiol, as well as estra-1,3,5(10)-triene-3,16β,17α-triol, is a minor and weak endogenous steroidal estrogen that is related to 17α-estradiol and estriol.[1][2] Along with estriol, 16β,17α-epiestriol has been detected in the urine of women during the late pregnancy stage.[2] It shows preferential affinity for the ERβ over the ERα.[3]

For other uses, see epiestriol (set index).
16β,17α-Epiestriol
Names
IUPAC name
Estra-1,3,5(10)-triene-3,16β,17α-triol
Systematic IUPAC name
(1S,2S,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,7-triol
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17-,18+/m1/s1
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@@H]([C@H]2O)O)CCC4=C3C=CC(=C4)O
Properties
C18H24O3
Molar mass 288.387 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

See also

References
  1. Vitamins and Hormones. Academic Press. 18 April 1972. pp. 233–. ISBN 978-0-08-086626-0.
  2. Ryō Satō; Ryūichi Katō (1982). Microsomes, drug oxidations, and drug toxicity. Japan Scientific Societies Press. p. 273. ISBN 978-0-471-87285-6.
  3. Zhu BT, Han GZ, Shim JY, Wen Y, Jiang XR (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.
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