Structure via PubChem · Public domain (PubChem)
estriol
Sign in to saveAlso known as Trimesta®, trihydroxyestrin, oestriol, 3,16alpha,17beta-trihydroxy-Delta(1,3,5)-estratriene, 16alpha-hydroxyestradiol, (16alpha,17beta)-estra-1,3,5(10)-triene-3,16,17-triol, Ortho-Gynest, Ovestinon
Estriol (E3), also spelled oestriol, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the others being estradiol and estrone. Levels of estriol in women who are not pregnant are almost undetectable. However, during pregnancy, estriol is synthesized in very high quantities by the placenta and is the most produced estrogen in the body by far, although circulating levels of estriol are similar to those of other estrogens due to a relatively high rate of metabolism and excretion. Relative to estradiol, both estriol and estrone have far w
Chemical data
- Formula
- C18H24O3
- Molecular weight
- 288.4 g/mol
- IUPAC name
- (8R,9S,13S,14S,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O
- InChIKey
- PROQIPRRNZUXQM-ZXXIGWHRSA-N
- XLogP
- 2.5
- Polar surface area
- 60.7 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
8,679 papers- The early history of estriol.Journal of steroid biochemistry · 1984
- [Presenile and senile vulvovaginitis. Topical hormonal treatment with estriol].Minerva ginecologica · 1991
- Bioavailability of oestriol.Acta endocrinologica · 1982
- Oestriol.The Journal of endocrinology · 1972
- Regiospecificity and stereospecificity of human UDP-glucuronosyltransferases in the glucuronidation of estriol, 16-epiestriol, 17-epiestriol, and 13-epiestradiol.Drug metabolism and disposition: the biological fate of chemicals · 2013
via PubMed
Wikidata facts
- Mass
- 288.173
Show 7 more facts
- chemical formula
- C₁₈H₂₄O₃
- isomeric SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O
- canonical SMILES
- CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
- Commons category
- Estriol
- MCN code
- 3003.39.33
- melting point
- 281
- defined daily dose
- 2
via Wikidata · CC0
~9 min read
Article
14 sectionsContents
- Biological activity
- Biochemistry
- Biosynthesis
- In non-pregnant women
- In pregnant women
- Distribution
- Metabolism
- Excretion
- Medical use
- Chemistry
- History
- Use in screening
- References
- Further reading
Estriol (E3), also spelled oestriol, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the others being estradiol and estrone. Levels of estriol in women who are not pregnant are almost undetectable. However, during pregnancy, estriol is synthesized in very high quantities by the placenta and is the most produced estrogen in the body by far, although circulating levels of estriol are similar to those of other estrogens due to a relatively high rate of metabolism and excretion. Relative to estradiol, both estriol and estrone have far weaker activity as estrogens.
In addition to its role as a natural hormone, estriol is used as a medication, for instance in menopausal hormone therapy; for information on estriol as a medication, see the estriol (medication) article.