15α-Hydroxyestradiol

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15α-Hydroxyestradiol
15alpha-hydroxyestradiol.svg
Names
Preferred IUPAC name
(1S,3S,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,3,7-triol
Other names
15α-OH-E2; 15α-Hydroxy-17β-estradiol; Estra-1,3,5(10)-triene-3,15α,17β-triol; 3,15α,17β-Trihydroxyestra-1,3,5(10)-triene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)17(18)15(20)9-16(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17-,18-/m1/s1
    Key: QVQMPLATUBCZMQ-GVLSGGHMSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1[C@H](C[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).

15α-Hydroxyestradiol (15α-OH-E2) is an endogenous estrogen which occurs during pregnancy.[1][2][3] It is structurally related to estriol (16α-hydroxyestradiol) and estetrol (15α-hydroxyestriol or 15α,16α-dihydroxyestradiol).

References[edit]

  1. ^ Lisboa BP, Goebelsmann U, Diczfalusy E (March 1967). "Isolation of 15-alpha-hydroxyoestradiol from human pregnancy urine". Acta Endocrinol. 54 (3): 467–72. doi:10.1530/acta.0.0540467. PMID 6071364.
  2. ^ Jirku H, Kadner S, Levitz M (October 1972). "Metabolism of 15alpha-hydroxyestradiol in human pregnancy". J. Clin. Endocrinol. Metab. 35 (4): 522–34. doi:10.1210/jcem-35-4-522. PMID 4559652.
  3. ^ Lee AJ, Kosh JW, Conney AH, Zhu BT (August 2001). "Characterization of the NADPH-dependent metabolism of 17beta-estradiol to multiple metabolites by human liver microsomes and selectively expressed human cytochrome P450 3A4 and 3A5". J. Pharmacol. Exp. Ther. 298 (2): 420–32. PMID 11454902.