16α-Hydroxyestrone

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
CAS Number	566-76-7
3D model (Jmol)	Interactive image
ChemSpider	103012
PubChem	115116
InChI 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
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H](C2=O)O)CCC4=C3C=CC(=C4)O
Properties
Chemical formula	C18H22O3
Molar mass	286.37 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

• 2-Hydroxyestradiol
• 16α-Hydroxy-DHEA
• 16α-Hydroxyandrostenedione

References

1. 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.