This document discusses estrogen, focusing on estradiol. It describes the main types of estrogen - estrone, estriol, and estradiol - and their functions. Estradiol is most potent during child-bearing years, while estriol is most prevalent during pregnancy. The document outlines the uses of estrogen in contraception and hormone replacement therapy. It discusses the history of estrogen research and future potential uses, and provides physical data and other names for estradiol.

1. ESTROGEN
With a Focus on Estradiol
by Noelani Fox
for the University of Texas
Organic Chemistry Lab

2. ESTROGENS
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Estrone Estriol
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Estradiol
* *
* *

3. FUNCTIONS
Transcription factor
 Mitogenesis
 Regulation of ovulation
Cumulative effects
 Antagonistic or agonistic

4. STAGES OF LIFE
 Estradiol – child-bearing years
 Most potent form
 Estriol – pregnancy
 Most prevalent form
 Weak except during
pregnancy
 Estrone - menopause

5. USES OF ESTROGEN
 Contraception
 Hormone replacement therapy (HRT)

6. USES OF ESTROGEN
 Contraception
 Estrogen-progestin
 daily
 DES (diethylstilbestrol)
 72 hours
 Hormone replacement therapy (HRT)

7. USES OF ESTROGEN
 Contraception
 Hormone replacement therapy (HRT)
 Vasomotor
 Acne and bleeding
 Osteoporosis prevention

8. PRECAUTIONS
DES and pregnancy
 Risk to daughters
 Vaginal adenomas, clear cell carcinoma
Long term HRT
Environmental concerns

9. PRECAUTIONS
DES and pregnancy
Long term HRT
• Women’s Health Initiative Study
 Endometrial carcinomas, breast cancer
 Stroke, thromboembolism
Environmental concerns

10. PRECAUTIONS
DES and pregnancy
Long term HRT
Environmental concerns
 Phthalate esters
 Breast and testicular cancer, male reproductive
tract disorders

11. HISTORY
Edward Adelbert Doisy
 Estrous cycle of mice
 Extract from sow ovaries
 Distilled urine from pregnant women
 Pig follicular fluid

12. FUTURE USES
Chemopreventive agent
 Colorectal cancer
 Schizophrenia therapy

13. PHYSICAL DATA
Molecular formula  Solubility
 3.60 mg/L @ 27°C
 C18H24O2
Molecular weight  Appearance
 272.38196 g/mol  White or slightly
yellow
Melting point  Powder, may form
small crystals
 173-179°C

14. OTHER NAMES
Common and trade names
 beta-Estradiol, 17beta-Estradiol, Dihydrofolliculin, Oestradiol,
Estrace, progynon, Dihydrotheelin, Dihydroxyestrin, and
Diogynets
 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

15. REFERENCES
 Cooke PS, Buchanan DL, Lubahn DB, Cunha GR, Mechanism of estrogen action: Lessons from the estrogen receptor- knockout mouse,
Biol Reprod, September 1998; 59(3): 470-475
 Simoni RD, Hill RL, Vaughan M, The discovery of estrone, estriol, and estradiol and the biochemical study of reproduction. The work of
Edward Adelbert Doisy, J Biol Chem, Jul 2002; 277: e17
 Whitehead SA, Nussey S (2001). Endocrinology: an integrated approach. Oxford: BIOS: Taylor & Francis. ISBN 1-85996-252-1.
 PubChem Compound at http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5757, accessed 2/15/2012
 Hazardous Substances Databank at http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+50-28-2, accessed
2/15/2012
 Tice LF, Estrogens: their function, uses and hazards. Part 2. Am Pharm, Feb 1978; 18(2): 30-33
 Rossouw J, Anderson GL, Prentice RL, LaCroix AZ, Kooperberg C, Stefanick ML, Jackson RD, Beresford SAA, Howard BV, Johnson KC,
Kotchen JM, Ockene J, Risks and benefits of estrogen plus progestin in healthy postmenopausal women: Principal results from
the Women’s Health Initiative Randomized Controlled Trial, JAMA, 2002; 288(3): 321-333
 Jobling S, Reynolds T, White R, Parker MG, Sumpter JP, A variety of environmentally persistent chemicals, including some phthalate
plasticizers, are weakly estrogenic, Environ Health Perspect, June 1995; 103(6): 582-587
 Protiva P, Cross HS, Hopkins ME, Kállay E, Bises G, Dreyhaupt E, Augenlicht L, Lipkin M, Lesser M, Livote E, Holt PR, Chemoprevention
of colorectal neoplasia by estrogen: potential role of vitamin D activity, Cancer Prev Res, January 2009; 2(1): 43-51
 Kulkarni J, Oestrogen — a new treatment approach for schizophrenia?, Med J Aust, February 2009; 190(4): S37-S38