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50-28-2

Basic Information
CAS No.: 50-28-2
Name: Estra-1,3,5(10)-triene-3,17-diol(17b)-
Article Data: 161
Cas Database
Molecular Structure:
Molecular Structure of 50-28-2 (Estra-1,3,5(10)-triene-3,17-diol(17b)-)
Formula: C18H24O2
Molecular Weight: 272.387
Synonyms: Estra-1,3,5(10)-triene-3,17-diol, (17b)-;Estra-1,3,5(10)-triene-3,17b-diol;Estrace;Estraderm;Estraderm MX;Estraldine;Estrapatch;Estreva;Estroclim;Estroclim 50;Estrogel HBF;Estropause;Evorel;FemSeven;Femogen;Follicyclin;Gelestra;Ginosedol;Gynoestryl;Macrodiol;Menorest;Menostar;Nordicol;Oestergon;Oestradiol;Oestrogel;Ovastevol;Ovocylin;Primofol;Profoliol;Dihydromenformon;Diogyn;Divigel;Encore;Epiestriol 50;Progynon;Progynon DH;Sandrena 1;Systen;Theelin, dihydro-;
EINECS: 200-023-8
Density: 1.17 g/cm3
Melting Point: 178-179 °C(lit.)
Boiling Point: 445.917 °C at 760 mmHg
Flash Point: 209.634 °C
Solubility: Soluble in dimethyl sulfoxide, ethanol , water, phosphate buffer saline, dimethyl formamide, acetone, dioxane and alkali hydroxides. Slightly soluble in vegetable oils.
Appearance: white crystalline powder
Hazard Symbols: ToxicT
Risk Codes: 60-61-45-63
Safety: 53-22-36/37/39-45
Transport Information: N/A
PSA: 40.46000
LogP: 3.60920
Synthetic route
901-93-9

estrone acetate

50-28-2

estradiol

Conditions
ConditionsYield
With diisobutylaluminium hydride; nickel dichloride In dichloromethane; toluene at -78℃; for 0.25h; Inert atmosphere;99%
1035-77-4

3-O-methyl-17β-oestradiol

50-28-2

estradiol

Conditions
ConditionsYield
With aluminium trichloride In ethanethiol for 0.5h; Ambient temperature;97.5%
With aluminium trichloride In ethanethiol for 0.5h; Ambient temperature;97.5%
With pyridine hydrochloride at 200℃; for 1h; Microwave irradiation; Ionic liquid;92%
53-16-7

Estrone

50-28-2

estradiol

Conditions
ConditionsYield
Stage #1: Estrone With sodium tetrahydroborate; sodium hydroxide In methanol; water for 0.75h;
Stage #2: With hydrogenchloride In methanol; water
97%
With silver tetrafluoroborate; diphenylsilane; C33H43ClN3ORh In dichloromethane at 40℃; for 24h; Reagent/catalyst; Glovebox; Sealed tube; diastereoselective reaction;95%
With potassium borohydride; Aliquat 336 In water at 60℃; for 1.5h;92%
14982-15-1

3-benzyloxyestra-1,3,5(10)-trien-17β-ol

50-28-2

estradiol

Conditions
ConditionsYield
With pyridine hydrochloride at 200℃; for 0.833333h; Microwave irradiation; Ionic liquid;97%
With palladium; acetic acid Hydrogenolyse;
With ethanol; sodium
With hydrogenchloride at 100℃;
69455-04-5

3,17β-bis(benzyloxy)estra-1,3,5(10)-triene

50-28-2

estradiol

Conditions
ConditionsYield
With aluminium trichloride; 1-dodecylthiol at 20℃; for 1h;97%
113680-55-0

(8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene

50-28-2

estradiol

Conditions
ConditionsYield
With aluminium trichloride; 1-dodecylthiol at 20℃; for 1h;96%
4954-14-7

(8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene

50-28-2

estradiol

Conditions
ConditionsYield
With aluminium trichloride; 1-dodecylthiol at 20℃; for 1h;95%
With aluminum tri-bromide In ethanethiol for 1h; Ambient temperature;94.3%
With aluminum tri-bromide In ethanethiol for 1h; Ambient temperature;94.3%
67-56-1

methanol

17046-60-5

17β-estradiol-3,17-disulfate potassium salt

50-28-2

estradiol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane; water at 60℃; for 72h; Product distribution; Further Variations:; Solvents; Temperatures; Hydrolysis;90%
10520-93-1

androsta-1,4-diene-3α/β,17β-diol

50-28-2

estradiol

Conditions
ConditionsYield
With n-butyllithium In hexane; toluene at 100℃; for 11h; Aromatisation;83.8%
28151-61-3

estradiol-17β 3-propargyl ether

50-28-2

estradiol

Conditions
ConditionsYield
With benzyltriethylammonium tetrathiomolybdate In acetonitrile at 28℃; for 48h;82%
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Consensus Reports

NTP 10th Report on Carcinogens. IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 , 1979,p. 279; IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 , 1974,p. 99.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

Specification

The Estradiol with the cas number 50-28-2, is also called (8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol named by IUPAC. Its' system names are (1) 17beta-Estradiol ; (2) Estra-1,3,5(10)-triene-3,17-diol (17beta)- ; (3) Estra-1,3,5(10)-triene-3,17-diol, (17beta)-. And it belongs to the following product categories: (1)Steroids; (2)Estrogen; (3)Hormone; (4)Analytical Chemistry; (5)Biochemistry; (6)Environmental Endocrine Disruptors; (7)Estradiol, etc. (Environmental Endocrine Disruptors); (8)Hydroxysteroids; (9)Intracellular receptor. It seems like off-white to pale yellow solid, and it is better to store Estradiol around 2-8°C. It is stable, however, it is incompatible with strong oxidizing agents.

Physical properties about 19-Norethisterone are: (1)ACD/LogP: 4.13 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 4.13 ; (4)ACD/LogD (pH 7.4): 4.13 ; (5)ACD/BCF (pH 5.5): 811.75 ; (6)ACD/BCF (pH 7.4): 810.7 ; (7)ACD/KOC (pH 5.5): 4208.86 ; (8)ACD/KOC (pH 7.4): 4203.38 ; (9)#H bond acceptors: 2 ; (10)#H bond donors: 2 ; (11)#Freely Rotating Bonds: 2 ; (12)Polar Surface Area: 18.46Å2 ; (13)Index of Refraction: 1.599 ; (14)Molar Refractivity: 79.5 cm3 ; (15)Molar Volume: 232.6 cm3 ; (16)Polarizability: 31.51 ×10-24cm3 ; (17)Surface Tension: 48.9 dyne/cm ; (18)Density: 1.17 g/cm3 ; (19)Flash Point: 209.6 °C ; (20)Enthalpy of Vaporization: 74.19 kJ/mol ; (21)Boiling Point: 445.9 °C at 760 mmHg ; (22)Vapour Pressure: 9.82E-09 mmHg at 25°C

Uses of Estradiol: It is a sex hormone, also called oestradiol. Estradiol is the predominant sex hormone present in females. It is also present in males, being produced as an active metabolic product of testosterone. In the female, estradiol acts as a growth hormone for tissue of the reproductive organs, supporting the lining of the vagina, the cervical glands, the endometrium, and the lining of the fallopian tubes. It enhances growth of the myometrium. Furthermore, the development of secondary sex characteristics in women is driven by estrogens, to be specific, estradiol. The effect of estradiol (and estrogens) upon male reproduction is complex. There is evidence that estradiol functions to prevent apoptosis of male sperm cells.

Besides, several studies have noted that sperm counts have been declining in many parts of the world and it has been postulated that this may be related to estrogen exposure in the environment. Suppression of estradiol production in a subpopulation of subfertile men may improve the semen analysis. There is evidence that estradiol has a profound effect on bone. Women past menopause experience an accelerated loss of bone mass due to a relative estrogen deficiency. Also, Estradiol has complex effects on the liver. It can lead to cholestasis. It affects the production of multiple proteins including lipoproteins, binding proteins, and proteins responsible for blood clotting. EspecialLy, Estrogen is considered to play a significant role in women’s mental health, with links suggested between the hormone, mood and well-being. Sudden drops or fluctuations in, or long periods of sustained low levels of estrogen may be correlated with significant mood-lowering. Clinical recovery from depression postpartum, perimenopause, and postmenopause was shown to be effective after levels of estrogen were stabilized and/or restored.

Production of  Estradiol. 1.During the reproductive years, most estradiol in women is produced by the granulosa cells of the ovaries by the aromatization of androstenedione (produced in the theca folliculi cells) to estrone, followed by conversion of estrone to estradiol by 17β-hydroxysteroid reductase. Smaller amounts of estradiol are also produced by the adrenal cortex, and (in men), by the testes. 2. Estradiol is not only produced in the gonads: in both sexes, precursor hormones, specifically testosterone, are converted by aromatization to estradiol. In particular, fat cells are active to convert precursors to estradiol, and will continue to do so even after menopause. Estradiol is also produced in the brain and in arterial walls.

When you are using this chemical, please be cautious about it as the following: It may impair fertility. And may cause harm or Possible risk of harm to the unborn child. Besides, it may also cause cancer. When you are using this product, wear suitable protective clothing, gloves and eye/face protection. In addition, avoid exposure - obtain special instructions before use. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure :
(1).SMILES: Oc1cc3c(cc1)[C@H]2CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]2CC3)C
(2).InChI:InChI=1/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1

Toxic information of Estradiol can be showed as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD subcutaneous > 300mg/kg (300mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 740, 1995.

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