Estrone

This article is about estrone as a hormone. For its use as a medication, see Estrone (medication).

Estrone
Names
IUPAC name
3-Hydroxyestra-1,3,5(10)-trien-17-one
Systematic IUPAC name
(3aS,3bR,9bS,11aS)-7-Hydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-1-one
Other names
Oestrone; E1
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.150 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1 ☒N
    Key: DNXHEGUUPJUMQT-CBZIJGRNSA-N ☒N
  • O=C4[C@]3(CC[C@@H]2c1ccc(O)cc1CC[C@H]2[C@@H]3CC4)C
Properties
C18H22O2
Molar mass 270.366 g/mol
Melting point 254.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Estrone (E1), also spelled oestrone, is a steroid, a weak estrogen, and a minor female sex hormone.[1] It is one of three major endogenous estrogens, the others being estradiol and estriol.[1] Estrone, as well as the other estrogens, are synthesized from cholesterol and secreted mainly from the gonads, though they can also be formed from adrenal androgens in adipose tissue.[2] Relative to estradiol, both estrone and estriol have far weaker activity as estrogens.[1] Estrone can be converted into estradiol, and serves mainly as a precursor or metabolic intermediate of estradiol.[1][3] It is both a precursor and metabolite of estradiol.[4][1]

In addition to its role as a natural hormone, estrone has been used as a medication, for instance in menopausal hormone therapy; for information on estrone as a medication, see the estrone (medication) article.

  1. ^ a b c d e Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  2. ^ Hornstein T, Schwerin JL (1 January 2012). Biology of Women. Cengage Learning. pp. 369–. ISBN 978-1-285-40102-7.
  3. ^ Cite error: The named reference KeepUtian2012 was invoked but never defined (see the help page).
  4. ^ Chervenak J (October 2009). "Bioidentical hormones for maturing women". Maturitas. 64 (2): 86–89. doi:10.1016/j.maturitas.2009.08.002. PMID 19766414.