File:Estradiol.svg · Wikimedia Commons · See Wikimedia Commons
17β-estradiol
Sign in to saveAlso known as E2, estrogen, oestrodiol, oestrogen, cis-estradiol, 17beta-estra-1,3,5(10)-triene-3,17-diol, (17beta)-estra-1,3,5(10)-triene-3,17-diol, 17beta-oestradiol
Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible for the development of female secondary sexual characteristics such as the breasts, widening of the hips and a female pattern of fat distribution. It is also important in the development and maintenance of female reproductive tissues such as the mammary glands, uterus and vagina during puberty, adulthood and pregnancy. It also has important effects in many
OverviewAI-generated
17β-estradiol is a chemical compound with the formula C₁₈H₂₄O₂. Its IUPAC name is (8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol. The substance has a mass of 272.178 and a weight of 272.4. It features a melting point of 200, a boiling point of 445.9, and a flash point of 209.6.
Physicochemical properties include a solubility of 3.6 and a water/octanol partition coefficient of 4.01. The compound has a pKa of 10.46, a topological polar surface area of 40.5, and a charge of 0. It contains two hydrogen bond donors and two hydrogen bond acceptors. The xlogp value is listed as 4.
Literature references for 17β-estradiol number 140,446. The subject is referenced by 2,070 other encyclopedia articles.
Synthesized by Vinony from 24 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C18H24O2
- Molecular weight
- 272.4 g/mol
- IUPAC name
- (8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O
- InChIKey
- VOXZDWNPVJITMN-ZBRFXRBCSA-N
- XLogP
- 4
- Polar surface area
- 40.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
140,446 papers- 17β-Estradiol Ameliorates Postoperative Cognitive Dysfunction in Aged Mice via miR-138-5p/SIRT1/HMGB1 Pathway.The international journal of neuropsychopharmacology · 2024
- Dihydrotestosterone and 17β-estradiol modulate TMJ osteoarthritis development and reveal sex-specific differences in pathogenesis.Scientific reports · 2025
- Oestrogenic Regulation of Mitochondrial Dynamics.International journal of molecular sciences · 2022
- From mitochondria to sarcopenia: role of 17β-estradiol and testosterone.Frontiers in endocrinology · 2023
- Actions of 17β-estradiol and testosterone in the mitochondria and their implications in aging.Ageing research reviews · 2013
via PubMed
~24 min read
Encyclopedic overview
27 sectionsContents
- Biological function
- Sexual development
- Reproduction
- Female reproductive system
- Male reproductive system
- Skeletal system
- Skin health
- Nervous system
- Gynecological cancers
- Cardiovascular system
- Other functions
- Biological activity
- Biochemistry
- Biosynthesis
- Distribution
- Metabolism
- Excretion
- Levels
- Measurement
- Ranges
- Medical use
- Chemistry
- Neuropsychopharmacology
- History
- Society and culture
- Etymology
- References
Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible for the development of female secondary sexual characteristics such as the breasts, widening of the hips and a female pattern of fat distribution. It is also important in the development and maintenance of female reproductive tissues such as the mammary glands, uterus and vagina during puberty, adulthood and pregnancy. It also has important effects in many other tissues including bone, fat, skin, liver, and the brain.
Though estradiol levels in males are much lower than in females, estradiol has important roles in males as well. Apart from humans and other mammals, estradiol is also found in most vertebrates and crustaceans, insects, fish, and other animal species.
Excerpted from Wikipedia’s “17β-estradiol” article, available under the CC BY-SA 4.0 licence.