2-Hydroxyestriol

2-Hydroxyestriol, also known as estra-1,3,5(10)-triene-2,3,16α,17β-tetrol, is an endogenous catechol estrogen and metabolite of estriol. It is a suspected carcinogen of carcinogenicity category 2.[1]

Selected biological properties of endogenous estrogens in rats
EstrogenERTooltip Estrogen receptor RBATooltip relative binding affinity (%)Uterine weight (%)UterotrophyLHTooltip Luteinizing hormone levels (%)SHBGTooltip Sex hormone-binding globulin RBATooltip relative binding affinity (%)
Control–100–100–
Estradiol (E2)100506 ± 20+++12–19100
Estrone (E1)11 ± 8490 ± 22+++ ?20
Estriol (E3)10 ± 4468 ± 30+++8–183
Estetrol (E4)0.5 ± 0.2 ?Inactive ?1
17α-Estradiol4.2 ± 0.8 ? ? ? ?
2-Hydroxyestradiol24 ± 7285 ± 8+b31–6128
2-Methoxyestradiol0.05 ± 0.04101Inactive ?130
4-Hydroxyestradiol45 ± 12 ? ? ? ?
4-Methoxyestradiol1.3 ± 0.2260++ ?9
4-Fluoroestradiola180 ± 43 ?+++ ? ?
2-Hydroxyestrone1.9 ± 0.8130 ± 9Inactive110–1428
2-Methoxyestrone0.01 ± 0.00103 ± 7Inactive95–100120
4-Hydroxyestrone11 ± 4351++21–5035
4-Methoxyestrone0.13 ± 0.04338++65–9212
16α-Hydroxyestrone2.8 ± 1.0552 ± 42+++7–24<0.5
2-Hydroxyestriol0.9 ± 0.3302+b ? ?
2-Methoxyestriol0.01 ± 0.00 ?Inactive ?4
Notes: Values are mean ± SD or range. ER RBA = Relative binding affinity to estrogen receptors of rat uterine cytosol. Uterine weight = Percentage change in uterine wet weight of ovariectomized rats after 72 hours with continuous administration of 1 μg/hour via subcutaneously implanted osmotic pumps. LH levels = Luteinizing hormone levels relative to baseline of ovariectomized rats after 24 to 72 hours of continuous administration via subcutaneous implant. Footnotes: a = Synthetic (i.e., not endogenous). b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: See template.
For other uses, see Hydroxyestriol.
2-Hydroxyestriol
Names
IUPAC name
Estra-1,3,5(10)-triene-2,3,16α,17β-tetrol
Systematic IUPAC name
(1R,2R,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,7,8-tetrol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C18H24O4/c1-18-5-4-10-11(13(18)8-16(21)17(18)22)3-2-9-6-14(19)15(20)7-12(9)10/h6-7,10-11,13,16-17,19-22H,2-5,8H2,1H3/t10-,11+,13-,16+,17-,18-/m0/s1
    Key: ZUGCDOZAVASBQT-SLVREZFOSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=CC(=C(C=C34)O)O
Properties
C18H24O4
Molar mass 304.386 g·mol−1
Hazards
GHS labelling:
H351
P201, P202, P281, P308+P313, P405, P501
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. "2-HYDROXYESTRIOL". National Center for Biotechnology Information. 17 December 2016. Archived from the original on 26 December 2016. Retrieved 26 December 2016.



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