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2-Hydroxyestrone (2-OHE1), also known as estra-1,3,5(10)-trien-2,3-diol-17-one, is an endogenous, naturally occurring catechol estrogen and a major metabolite of estrone and estradiol.[1][2][3] It is formed irreversibly from estrone in the liver and to a lesser extent in other tissues via 2-hydroxylation mediated by cytochrome P450 enzymes, mainly the CYP3A and CYP1A subfamilies.[1][3] 2-OHE1 is the most abundant catechol estrogen in the body.[3] It is not significantly uterotrophic in bioassays, whereas other hydroxylated estrogen metabolites including 2-hydroxyestradiol, 16α-hydroxyestrone, estriol (16α-hydroxyestradiol), 4-hydroxyestradiol, and 4-hydroxyestrone all are.[1][4]

2-Hydroxyestrone
2-Hydroxyestrone.svg
Names
IUPAC name
(8R,9S,13S,14S)-2,3-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
Other names
2-OHE1; 2,3-Dihydroxyestra-1,3,5(10)-trien-17-one; Estra-1,3,5(10)-trien-2,3-diol-17-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.164.607
KEGG
UNII
Properties
C18H22O3
Molar mass 286.371 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 alsoEdit

ReferencesEdit

  1. ^ a b c Oettel M, Schillinger E (6 December 2012). Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens. Springer Science & Business Media. p. 227. ISBN 978-3-642-58616-3.
  2. ^ Rakel D (2012). Integrative Medicine. Elsevier Health Sciences. pp. 338–. ISBN 1-4377-1793-4.
  3. ^ a b c Buchsbaum HJ (6 December 2012). The Menopause. Springer Science & Business Media. pp. 64–65. ISBN 978-1-4612-5525-3.
  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". Journal of the Society for Gynecologic Investigation. 7 (3): 175–83. doi:10.1016/s1071-5576(00)00049-6. PMID 10865186.

External linksEdit