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

2. ESTROGENS**Estrone Estriol*Estradiol* ** * 3. FUNCTIONSTranscription factor Mitogenesis Regulation of ovulationCumulative effects Antagonistic or agonistic 4. STAGES OF LIFE Estradiol child-bearing years Most potent form Estriol pregnancy Most prevalent form Weak except duringpregnancy 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. PRECAUTIONSDES and pregnancy Risk to daughters Vaginal adenomas, clear cell carcinomaLong term HRTEnvironmental concerns 9. PRECAUTIONSDES and pregnancyLong term HRT Womens Health Initiative Study Endometrial carcinomas, breast cancer Stroke, thromboembolismEnvironmental concerns 10. PRECAUTIONSDES and pregnancyLong term HRTEnvironmental concerns Phthalateesters Breast and testicular cancer, male reproductive tract disorders 11. HISTORYEdward Adelbert Doisy Estrous cycle of mice Extract from sow ovaries Distilled urine from pregnant women Pig follicular fluid 12. FUTURE USESChemopreventive agent Colorectal cancer Schizophrenia therapy 13. PHYSICAL DATAMolecular formula Solubility 3.60 mg/L @ 27C C18H24O2Molecular weight Appearance 272.38196 g/mol White or slightlyyellowMelting point Powder, may formsmall crystals 173-179C 14. OTHER NAMESCommon and trade names beta-Estradiol, 17beta-Estradiol, Dihydrofolliculin, Oestradiol,Estrace, progynon, Dihydrotheelin, Dihydroxyestrin, andDiogynets 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 ofEdward 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, accessed2/15/2012 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 fromthe Womens 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 phthalateplasticizers, are weakly estrogenic, Environ Health Perspect, June 1995; 103(6): 582-587 Protiva P, Cross HS, Hopkins ME, Kllay E, Bises G, Dreyhaupt E, Augenlicht L, Lipkin M, Lesser M, Livote E, Holt PR, Chemopreventionof 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