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16α-Hydroxyestrone

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16α-Hydroxyestrone
Names
IUPAC name
(8R,9S,13S,14S,16R)-3,16-Dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
Other names
Hydroxyestrone; 16-Hydroxyestrone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.164.941 Edit this at Wikidata
  • InChI=1S/C18H22O3/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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H](C2=O)O)CCC4=C3C=CC(=C4)O
Properties
C18H22O3
Molar mass 286.371 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

16α-Hydroxyestrone (16α-OH-E1), or hydroxyestrone, also known as estra-1,3,5(10)-trien-3,16α-diol-17-one, is an endogenous steroidal estrogen and a major metabolite of estrone, as well as an intermediate in the biosynthesis of estriol.[1][2] It is a potent estrogen similarly to estrone, and it has been suggested that the ratio of 16α-hydroxyestrone to 2-hydroxyestrone, the latter being much less estrogenic in comparison and even antiestrogenic in the presence of more potent estrogens like estradiol, may be involved in the pathophysiology of breast cancer.[1] Conversely, 16α-hydroxyestrone may help to protect against osteoporosis.[1] In contrast to estradiol, the binding of 16α-hydroxyestrone to the estrogen receptor is, uniquely, covalent and irreversible, and genotoxicity and aberrant hyperproliferations may result.[3] A diacetate ester of 16α-hydroxyestrone, hydroxyestrone diacetate, has been marketed and is used medically as an estrogen in Europe.[4][5]

See also

References

  1. ^ a b c David Rakel (2012). Integrative Medicine. Elsevier Health Sciences. pp. 338–339. ISBN 1-4377-1793-4.
  2. ^ Vitamins and Hormones. Academic Press. 7 September 2005. pp. 282–. ISBN 978-0-08-045978-3.
  3. ^ Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens. Springer Science & Business Media. pp. 252–. ISBN 978-3-642-58616-3.
  4. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1250–. ISBN 978-3-88763-075-1.
  5. ^ Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 289–. ISBN 978-3-7692-2114-5.


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