Estrogens from acetate

It has recently been clearly demonstrated that estrogens can arise (1) from acetate, (2) by conversion of cholesterol and of progesterone, and (3) by aromatization of neutral Cig- and Cjs-steroids. Evidence has been pre-... 

Reaction of estrone (2) with an excess of the lithium reagent from 3-iodofuran gives intermediate diol 3. The stereochemical assignment follows from the well-known propensity of steroids for attack from the less-hindered backside (a) of the molecule. Acylation of 3 with acetic anhydride then affords the estrogen estrvfurate (4).1... 

Tan D, Haines CJ, Limpaphayom KK, et al. Relief of vasomotor symptoms and vaginal atrophy with three doses of conjugated estrogens and medroxyprogesterone acetate in postmenopausal Asian women from 11 countries the Pan-Asia menopause (PAM) study. Maturitas. 2005 52 35-51. 

Fig. 8.19. Coordination ion spray mass spectrum of estradiol extracted from the reversed-phase CEC—CIS-MS separation of estrogenic compounds. Column, 250 x 0.1 mm i.d. packed with 3 pm GROM-SIL ODS-O AB eluent, 4 mmol/1 ammonium acetate, pH 9.0, 50% acetonitrile applied pressure, 8 MPa applied voltage, 15 kV detection, ESI-MS, 0.85 s/spectrum sheath liquid, 100 pg/ml aqueous silver nitrate, 3 pl/min mass spectrum extracted from a reconstructed ion chromatogram of the separation of estriol, estradiol, equiline, and estrone. (Reproduced from ref. [104] with permission of Wiley-VCh).

Femtrace Estrodiol acetate 0.45, 0.9, 1.8 mg Tablet Vasomotor symptom from menopause Estrogen receptor Povidone, lactose monohydrate, MCC, croscarmellose Na, silicon dioxide, magnesium stearate Warner Chilcott... 

A study concerning the yields of fluorination by acid decomposition of piperidinotriazenes from several anilines with hydrogen fluoride (anhyd HF, coned aq HF, or HF, pyridine) in various solvents, such as tetrahydrofuran, benzene, dichloromethane, and acetic acid, was carried out in order to establish the best reaction conditions for the [ F]fluorine labeling of estrogens. Hence, 2 -fluorohexcstrol dimethyl ether (4) can be obtained from triazene 3 using 49% aqueous hydrogen fluoride. ... 

---