2-Hydroxyestradiol

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2-Hydroxyestradiol
Names
IUPAC name
Estra-1,3,5(10)-triene-2,3,17β-triol
Systematic IUPAC name
(1S,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,7,8-triol
Other names
2-OHE2
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.160.393 Edit this at Wikidata
UNII
  • InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=C(C=C34)O)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).

2-Hydroxyestradiol (2-OHE2), also known as estra-1,3,5(10)-triene-2,3,17β-triol, is an

positional isomer of estriol.[1]

Biosynthesis

Transformation of estradiol to 2-hydroxyestradiol is a major

sulfonation) of 2-hydroxyestradiol followed by urinary excretion.[1]

Biological activity

Estrogenic activity

2-Hydroxyestradiol has approximately 7% and 11% of the

G protein-coupled estrogen receptor (GPER) (100–1,000 μM).[5]

Selected biological properties of endogenous estrogens in rats
Estrogen
RBA
Tooltip relative binding affinity (%)		 Uterine weight (%)
Uterotrophy
 LHTooltip Luteinizing hormone levels (%)
RBA
Tooltip relative binding affinity (%)
Control – 100 – 100 –
Estradiol (E2) 100 506 ± 20 +++ 12–19 100
Estrone (E1) 11 ± 8 490 ± 22 +++ ? 20
Estriol (E3) 10 ± 4 468 ± 30 +++ 8–18 3
Estetrol (E4) 0.5 ± 0.2 ? Inactive ? 1
17α-Estradiol 4.2 ± 0.8 ? ? ? ?
2-Hydroxyestradiol 24 ± 7 285 ± 8 +b 31–61 28
2-Methoxyestradiol 0.05 ± 0.04 101 Inactive ? 130
4-Hydroxyestradiol 45 ± 12 ? ? ? ?
4-Methoxyestradiol 1.3 ± 0.2 260 ++ ? 9
4-Fluoroestradiola 180 ± 43 ? +++ ? ?
2-Hydroxyestrone 1.9 ± 0.8 130 ± 9 Inactive 110–142 8
2-Methoxyestrone 0.01 ± 0.00 103 ± 7 Inactive 95–100 120
4-Hydroxyestrone 11 ± 4 351 ++ 21–50 35
4-Methoxyestrone 0.13 ± 0.04 338 ++ 65–92 12
16α-Hydroxyestrone 2.8 ± 1.0 552 ± 42 +++ 7–24 <0.5
2-Hydroxyestriol 0.9 ± 0.3 302 +b ? ?
2-Methoxyestriol 0.01 ± 0.00 ? Inactive ? 4
Notes: Values are mean ± SD or range. ER RBA =
endogenous
). b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: See template.

Catecholaminergic activity

2-Hydroxyestradiol is a

micromolar range.[6][8]

2-Hydroxyestradiol has been found to increase prolactin secretion when administered

2-hydroxyestrone, which inhibits tyrosine hydroxylase similarly to 2-hydroxyestradiol, showed no such increase in prolactin secretion.[9] The researchers concluded that the most likely explanation was that the increase was mediated by the estrogenic activity of 2-hydroxyestradiol, as similar increments in prolactin levels had been observed with estradiol.[9] In any case, these findings argue against the notion of major interactions of 2-hydroxyestradiol with the dopamine system.[9]

Genotoxicity

2-Hydroxyestradiol, as well as 2-hydroxyestrone and

tumor growth and angiogenesis, and this may contribute as well.[1]

Production of 2-methoxyestradiol

2-Hydroxyestradiol has been identified as a

catechol O-methyltransferase in the liver.[10] 2-Methoxyestradiol is not estrogenic but is a potent angiogenesis inhibitor and agonist of the GPER with potential therapeutic implications in cancer.[11]

Antioxidant activity

Similarly to other steroidal estrogens, 2-hydroxyestradiol is an antioxidant, but the catechol estrogens (2- and 4-hydroxylated estrogens) like 2-hydroxyestradiol are considered to be the most potent in terms of antioxidant activity.[12][dubious – discuss]

History

2-Hydroxyestradiol was identified as a metabolite of estradiol in 1960.[13]

References

  1. ^
    PMID 9472688
    .
  2. PMID 9048584
    .
  3. S2CID 27048999
    .
  4. S2CID 42692912
    .
  5. PMID 26023144
    .
  6. ^
    PMID 447670
    .
  7. S2CID 25129158
    .
  8. ^
    S2CID 20391880
    .
  9. ^
    PMID 6772666
    .
  10. S2CID 38176855
    .
  11. PMID 26585123
    .
  12. ISBN 978-0-203-30393-1
    .
  13. PMID 379882
    .
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