This document discusses estrogen, including its structure, types, and biosynthesis. There are three main naturally occurring forms of estrogen: estrone, estradiol, and estriol. Estrone was the first estrogen to be isolated from pregnant women's urine. Estradiol is the most biologically active form and the main estrogen produced in premenopausal women. Estrogen structures contain steroid nuclei and are synthesized from cholesterol through a series of hydroxylation and aromatization reactions in various tissues like the ovaries and liver.

1. Estrogen
(Steroidal hormone)

2. Submitted to:
Prof.Dr. Abida
SUBMITTED BY:
Sidra (MP- CHEM- 4)
2020-2022
Organic chemistry (1st Semester)
The Women University Multan
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3. contents:
1. Introduction of Estrogen
2. Structure of estrogen
2.1 Types of estrogen
2.1.1 Estrone(E1)
2.1.2 Estriol(E2)
2.1.3 Estradiol(E3)
3. Biosynthesis of estrogen
4. Reference
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4. 1.Introduction of estrogen:
• The word estrogen derives from Ancient Greek. It is derived from “
oestros ” (a periodic state of sexual activity in female mammals ), and
genos (generating).
• Estrogens are synthesized in all vertebrates as well as some insects.
The three major naturally occurring forms of estrogen in women are
estrone (E1), estradiol (E2), and estriol (E3).
• In addition to their role as natural hormones, estrogens are used as
medications, for instance in menopausal hormone therapy and
hormonal birth control.

5. 2.Structure of estrogen:
Structure of estrogen is cleared by discussion of its main types .
2.1 Types of estrogen
There are three types given below:
2.1.1 Estrone
2.1.2 Estriol
2.1.3 Estradiol
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6. 2.1.1 Estrone:
• Butenandt and Doisy independently isolated the active substance estrone
from the urine of pregnant women. It is the first known member of sex
hormones, and soon after its discovery two other hormones were isolated,
estriol and estradiol.
• Estrone , m.p. 259 ᵒ , has the molecular formula C18H22O2.
• It behaves as a ketone ( forms an oxime,) and contains one hydroxyl group (it
forms a monoacetate and a monomethyl ether). Furthermore, this hydroxyl
group is phenolic , since estrone couples with diazonium salts in alkaline.

7. • The X-ray analysis of estrone also indicates the presence of the steroid nucleus,
and at the same time showed that the keto group and the hydroxyl group are at
the opposite ends of molecule.
• The presence of one benzene ring in the structure of estrone is supported by
measurements of the molecular refractivity and the UV absorption spectrum.
Chemistry of Estrone:
When methyl ether of estrone I is treated with methyl magnesium iodide,
compound II is obtained. When II is dehydrated with potassium hydrogen
sulphate to III, this catalytically reduced to IV and then to IV distilled with
selenium, the product is 7-methoxy-3`: 3`-dimethyl-1:2-
cyclopentenophenanthrene, V. The formation of V can be explained only if there is
a keto group at position 17 and an angular methyl group at position 13.
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9. The structure of V has been confirmed by synthesis. The final structure of
estrone :
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10. 2.1.2 Estriol:
General formula of estriol is C18H24O3. Its melting point is 281º, was isolated from
human pregnancy urine by Marrian 1930. It forms a triacetate, three hydroxal groups
are present. One of which is phenolic and other two secondary alcoholic ,since
produced by oxidation of diketone. X-ray analysis indicate that two hydroxal groups
are in vicinal position When estriol fused with KOH marrianolic acid(II) and this on
dehydrogenation with selenium to form hydroxy dimethyl phenanthrene (III).
Fig 2.1.2 Structure of estriol
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11. Synthesis of Estriol:
Leeds et al(1954) have converted estrone to estriol by a simpler method.
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12. 2.1.3 Estradiol:
This is a type of estrogen hormone. It’s general formula is C18H24O2. There are two
stereoisomeric estradiol's, α isomer and ß isomer.
Synthesis of Estradiol:
Vellus et al(1960) have synthesized estradiol using starting material 6-methoxy-1-
tetralone;this is therefore a complete synthesis of this hormone. α estradiol was first
obtained by reduction of estrone but latter it was isolated from the ovaries of sows.
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13. Α estradiol is much more active than estrone. Whereas ß estradiol is less active. It
appears that estradiol is the real hormone and that estrone and estriol are metabolic
products.
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14. 3. Biosynthesis of estrogen:
• Estrogen are synthesized in a variety of tissues. Cholesterol is precursor of
biosynthesis of estrogen. Cholesterol is metabolized to pregnenolone is than
converted to progesterone in the presence of an isomerase enzyme. Within
ovarian follicle, the testosterone is formed.
• Estrogen are form by aromatization of androgen in a complex process that
include 3 hydroxylation steps each of which required oxygen molecule and
NADPH.17ß-estradiol is formed from testosterone that oxidized to estrone in
the liver, it may be further hydrated to estriol.
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Fig 3.1 Biosynthesis of estrogen

16. 4. Reference:
• I . L . FINAR , Organic chemistry, volume two(398-409).
• www.biologydiscussion .com
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