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LEAPChem Highlights Estradiol today!
Basic
Information of Estradiol
Chemical Name: Estradiol
Cas No.: 50-28-2
Molecular Formula: C18H24O2
Chemical Structure:
Estradiol (E2),
also spelled oestradiol, is an estrogen steroid hormone and the major female
sex hormone. It is involved in the regulation of the estrous and menstrual
female reproductive cycles. Estradiol is responsible for the development of
female secondary sexual characteristics such as the breasts, widening of the
hips, and a feminine pattern of fat distribution in women and is 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 men are much lower compared to
those in women, estradiol has important roles in men as well. Aside from humans
and other mammals, estradiol is also found in most vertebrates and crustaceans,
insects, fish, and other animal species.
Estradiol is produced especially within the
follicles of the ovaries, but also in other tissues including the testicles, the
adrenal glands, fat, liver, the breasts, and the brain. Estradiol is produced
in the body from cholesterol through a series of reactions and intermediates.
The major pathway involves the formation of androstenedione, which is then
converted by aromatase into estrone and is subsequently converted into
estradiol. Alternatively, androstenedione can be aromatized into testosterone,
which can then be converted into estradiol. Upon menopause in women, production
of estrogens by the ovaries stops and estradiol levels decrease to very low
levels.
Estradiol acts primarily as an agonist of
the estrogen receptor (ER), a nuclear steroid hormone receptor. There are two
subtypes of the ER, ERα and ERβ, and estradiol potently binds to and activates
both of these receptors. The result of ER activation is a modulation of gene
transcription and expression in ER-expressing cells, which is the predominant
mechanism by which estradiol mediates its biological effects in the body.
Estradiol also acts as an agonist of membrane estrogen receptors (mERs), such
as GPER (GPR30), a recently discovered non-nuclear receptor for estradiol, via
which it can mediate a variety of rapid, non-genomic effects. Unlike the case
of the ER, GPER appears to be selective for estradiol, and shows very low
affinities for other endogenous estrogens, such as estrone and estriol.[39]
Additional mERs besides GPER include ER-X, ERx, and Gq-mER.
Estradiol, like other steroid hormones, is
derived from cholesterol. After side chain cleavage and using the Δ5 or the Δ4-
pathway, androstenedione is the key intermediary. A portion of the
androstenedione is converted to testosterone, which in turn undergoes
conversion to estradiol by aromatase. In an alternative pathway,
androstenedione is aromatized to estrone, which is subsequently converted to
estradiol via 17β-hydroxysteroid dehydrogenase (17β-HSD).
Estradiol is an estrane steroid. It is also
known as 17β-estradiol (to distinguish it from 17α-estradiol) or as
estra-1,3,5(10)-triene-3,17β-diol. It has two hydroxyl groups, one at the C3
position and the other at the 17β position, as well as three double bonds in
the A ring. Due to its two hydroxyl groups, estradiol is often abbreviated as
E2. The structurally related estrogens, estrone (E1), estriol (E3), and estetrol
(E4) have one, three, and four hydroxyl groups, respectively.
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If you are interested in Estradiol, click here to send an inquiry!
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References:
https://en.wikipedia.org/wiki/Estradiol
https://www.ncbi.nlm.nih.gov/pubmed/11511861
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2754262/
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