Interesting facts from the world of organic chemistry
Derivatives - alcohols:
Estradiol
Estradiol, or otherwise also 17-β-estradiol, oestradiol or E2, belongs together with estrone and estriol to the group of female sex hormones. The designation E2 is used because it has two hydroxyl groups –OH in its structure. Estrone, on the other hand, has only one OH group (hence E1) and estriol has three (which is why it is sometimes referred to as E3).
The action of these hormones is very diverse. With estradiol, the effect on the growth of the female reproductive organs is considered key. The intensity of estradiol action (the so-called estrogenic effect) is the highest among estradiol, estrone and estriol. Even ten times higher than in the case of estrone and approximately 80 times higher than in the case of estriol.
Estradiol production increases during pregnancy due to formation in the placenta. During the menstrual cycle, it is produced and released by growing follicles (a follicle is a fluid-filled cavity in the ovary in which an egg matures). Thanks to the positive feedback of the hypothalamo-pituitary system, it participates in the initiation of ovulation.
Similar to the biosynthesis of progesterone, testosterone or estrone, the biosynthesis of these hormones is based on cholesterol. The cholesterol molecule represents a basic carbon skeleton, which is usually modified in several steps. The individual steps are shown schematically in the figure below.
Picture above: Schema of conversion of testosterone to estradiol in men body.
If the starting compound is testosterone, the action of the aromatase enzyme leads directly to the formation of estradiol. The scheme of this transformation is shown in the figure below.
Picture above: Scheme of the direct synthesis of estradiol from testosterone.
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