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lecture 26.2 - Organic Chemistry William H Brown...

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26- 26-1 Organic Organic Chemistry Chemistry William H. Brown William H. Brown Christopher S. Foote Christopher S. Foote Brent L. Iverson Brent L. Iverson
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26- 26-2 Lipids Lipids Chapter 26 Chapter 26
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26- 26-3 Steroids Steroids Steroids: Steroids: a group of plant and animal lipids that have this tetracyclic ring structure The features common to the ring system of most naturally occurring steroids are illustrated on the next screen A B C D
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26- 26-4 Steroids Steroids the fusion of rings is trans and each atom or group at a ring junction is axial the pattern of atoms or groups along the ring junctions is nearly always trans -anti- trans -anti- trans the steroid system is nearly flat and quite rigid most have have axial methyl groups at C-10 and C-13 H CH 3 H H CH 3 H
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26- 26-5 Cholesterol Cholesterol H 3 C HO H 3 C H H H
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26- 26-6 Androgens Androgens Androgens - male sex hormones synthesized in the testes responsible for the development of male secondary sex characteristics Androsterone Testosterone O H OH H H 3 C H H H 3 C H 3 C H H H 3 C H O HO
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26- 26-7 Synthetic Anabolic Steroids Synthetic Anabolic Steroids a way to increase the testosterone concentration is to use a prohormone, which the body converts to testosterone; for example “andro” O H 3 C H H H H 3 C HO CH 3 O H 3 C CH 3 H H 3 C OH H H H O H 3 C H H 3 C H H O O H CH 3 H 3 C OC(CH 2 ) 8 CH 3 H H O Methandrostenolone Methenolone Nandrolone decanoate 4-Androstene-3,17-dione (andro)
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26- 26-8 Estrogens Estrogens Estrogens - female sex hormones synthesized in the ovaries responsible for the development of female secondary sex characteristics and control of the menstrual cycle Progesterone Estrone H 3 C H H H 3 C H C= O H O CH 3 O HO H H H H 3 C
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26- 26-9 Synthetic Estrogens Synthetic Estrogens Progesterone-like analogs are used in oral contraceptives "Nor" refers to the absence  of a methyl group here.   The methyl group is present  in ethindrone Norethindrone H 3 C H H H O H HO C CH
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