Conditions | Yield |
---|---|
With diisobutylaluminium hydride; nickel dichloride In dichloromethane; toluene at -78℃; for 0.25h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
3-benzyloxyestra-1,3,5(10)-trien-17β-ol
estradiol
Conditions | Yield |
---|---|
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℃; |
3,17β-bis(benzyloxy)estra-1,3,5(10)-triene
estradiol
Conditions | Yield |
---|---|
With aluminium trichloride; 1-dodecylthiol at 20℃; for 1h; | 97% |
(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
estradiol
Conditions | Yield |
---|---|
With aluminium trichloride; 1-dodecylthiol at 20℃; for 1h; | 96% |
(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
estradiol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In 1,4-dioxane; water at 60℃; for 72h; Product distribution; Further Variations:; Solvents; Temperatures; Hydrolysis; | 90% |
androsta-1,4-diene-3α/β,17β-diol
estradiol
Conditions | Yield |
---|---|
With n-butyllithium In hexane; toluene at 100℃; for 11h; Aromatisation; | 83.8% |
estradiol-17β 3-propargyl ether
estradiol
Conditions | Yield |
---|---|
With benzyltriethylammonium tetrathiomolybdate In acetonitrile at 28℃; for 48h; | 82% |
estradiol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 45℃; for 24h; | 81% |
1β-hydroxy-3-trimethylsilylestra-1,3,5(10)-triene
estradiol
Conditions | Yield |
---|---|
With Pb(trifluoroacetate)4; trifluoroacetic acid at 20℃; for 0.5h; Oxidation; | 80% |
(8R,9S,13S,14S,17S)-3-(4-methoxybenzyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol
estradiol
Conditions | Yield |
---|---|
With proton-exchanged montmorillonite In dichloromethane at 20℃; | 78% |
Conditions | Yield |
---|---|
With Hexamethyldisiloxane; toluene-4-sulfonic acid In methanol; dichloromethane at -30 - 38℃; | A 72.8% B n/a |
chloro-trimethyl-silane
2,4-dibromo-3,17β-bis(trimethylsiloxy)estra-1,3,5(10)-triene
A
estradiol
B
2-(trimethylsilyl)estra-1,3,5(10)-triene-3,17β-diol
C
4-(trimethylsilyl)estra-1,3,5(10)-triene-3,17β-diol
Conditions | Yield |
---|---|
With methanol; sodium; potassium carbonate 1.) xylene, 1 h, 110 deg C, 2.) 1 h, 20 deg C; Yields of byproduct given; | A n/a B 68% C n/a |
With methanol; sodium; potassium carbonate 1.) xylene, 1 h, 110 deg C, 2.) 1 h, 20 deg C; Yield given; | A n/a B 68% C n/a |
sodium methylate
3,17β-di-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>estra-1,3,5(10)-triene
A
estradiol
B
17β-<2,6-difluoro-3,5-dimethoxy-4-(trifluoromethyl)phenoxy>estra-1,3,5(10)-trien-3-ol
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 10℃; for 2h; | A 4% B 68% |
10β-Hydroxy-17β-(benzoyloxy)-19-norandrost-4-en-3-one
estradiol
Conditions | Yield |
---|---|
With potassium hydroxide In methanol for 1h; Heating; | 68% |
Conditions | Yield |
---|---|
With copper(l) iodide; sodium methylate In methanol; N,N-dimethyl-formamide | A 50% B 3% |
2-bromoestradiol
sodium methylate
A
estradiol
B
2-Methoxyestradiol
Conditions | Yield |
---|---|
With copper(l) iodide In methanol; N,N-dimethyl-formamide | A 50% B 3% |
Conditions | Yield |
---|---|
With copper(l) iodide; sodium methylate In methanol; N,N-dimethyl-formamide | A 50% B 3% |
chloro-trimethyl-silane
3-methoxy-17β-(trimethylsiloxy)estra-1,3,5(10)-triene
A
estradiol
B
D-1α-(trimethylsilyl)-17β-hydroxyestr-5(10)-en-3-one
C
D-1α-(trimethylsilyl)-17β-hydroxyestr-4-en-3-one
Conditions | Yield |
---|---|
With 2O deg C; DME+HMPA; lithium; acetic acid Product distribution; oth. solvent; | A 9.9% B 37% C 13% D 9.9% |
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydroxide In water at 70℃; electrolysis; | A n/a B 30% |
With tetra(n-butyl)ammonium hydroxide In water electrolysis; | A n/a B 30% |
Conditions | Yield |
---|---|
With cytosyl normal human prostate for 1h; Product distribution; Ambient temperature; | A 9.6% B 8.9% |
6-dehydro-19-nortestosterone acetate
allyl-trimethyl-silane
A
estradiol
B
17β-acetoxy-7α-allyloestr-4-en-3-one
Conditions | Yield |
---|---|
With diethylaluminium chloride In dichloromethane at -15℃; for 2.5h; Product distribution; other reagents and products; other solvents and temperatures; | A 2% B 2% |
Conditions | Yield |
---|---|
at 370 - 390℃; | |
at 370 - 390℃; |
Conditions | Yield |
---|---|
With propan-1-ol; sodium |
Conditions | Yield |
---|---|
at 370 - 390℃; | |
at 370 - 390℃; |
Conditions | Yield |
---|---|
at 370 - 390℃; | |
at 370 - 390℃; |
9,10-dihydrophenanthrene
1-dehydrotestosterone
A
estradiol
B
4-methyl-estratriene-(1.3.5(10))-diol-(1.17β)
Conditions | Yield |
---|---|
at 390℃; |
Conditions | Yield |
---|---|
Isolierung aus dem Harn von Maennern nach Injektion von (+)-O-Acetyl-oestron; |
estradiol
acetic anhydride
estradiol-3,17-diacetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 0.00833333h; microwave irradiation; | 100% |
With pyridine at 20℃; for 16h; Cooling with ice; | 98% |
With pyridine In dichloromethane at 20℃; for 12h; | 96% |
3,4-dihydro-2H-pyran
estradiol
3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 3h; | 100% |
With 2,4,6-Trinitrophenol In benzene | 98% |
With toluene-4-sulfonic acid | 94% |
Conditions | Yield |
---|---|
for 0.5h; Heating; | 100% |
estradiol
para-nitrophenyl triflate
3-(trifluoromethanesulfonyl)-β-estradiol
Conditions | Yield |
---|---|
With potassium carbonate In pentane for 2h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) In tert-butyl alcohol at 130℃; for 20h; | 100% |
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) In tert-butyl alcohol for 20h; Reflux; | 100% |
With polystyrene-supported(cathecholato) oxoRe cat. act by iPrOH; dimethyl sulfoxide In toluene for 4h; Heating; Dean-Stark apparatus; | 98% |
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran; dichloromethane at -5 - 20℃; under 760.051 Torr; for 3h; | 100% |
Conditions | Yield |
---|---|
Stage #1: estradiol With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: tert-butyl 2-(4-nitrophenyl)diazenecarboxylate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 100% |
Stage #1: estradiol With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: tert-butyl 2-(4-nitrophenyl)diazenecarboxylate In N,N-dimethyl-formamide Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With rubidium fluoride In acetonitrile at 80℃; for 1h; | 100% |
estradiol
<2,4-2H2>-1,3,5(10)-estratriene-3,17β-diol
Conditions | Yield |
---|---|
With perchloric acid; chloroform-d1; d(4)-methanol at 75℃; for 144h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With C12F18O13Zn4 for 40h; Reflux; Inert atmosphere; chemoselective reaction; | 99% |
With sodium hydrogen sulfate; silica gel In hexane at 67℃; for 72h; | 59% |
Conditions | Yield |
---|---|
With potassium carbonate at 90℃; for 3h; | 98% |
Conditions | Yield |
---|---|
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 90℃; for 24h; | 98% |
chloro-trimethyl-silane
estradiol
3,17β-bis(trimethylsiloxy)estra-1,3,5(10)-triene
Conditions | Yield |
---|---|
With 1,1,1,3,3,3-hexamethyl-disilazane In benzene for 5h; Heating; | 97% |
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetone Reflux; | 97% |
With potassium carbonate In acetone Heating; | 93% |
With potassium carbonate In acetone for 18h; Reflux; | 93% |
estradiol
chloromethyl methyl ether
(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
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Heating; | 97% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 80℃; for 3h; | 97% |
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Heating; | 96% |
Conditions | Yield |
---|---|
With sodium carbonate In methanol for 64h; Reflux; Inert atmosphere; | 97% |
With potassium carbonate In acetonitrile for 15h; Heating; | 94% |
With potassium carbonate | |
With potassium carbonate | |
With potassium carbonate |
estradiol
p-toluenesulfonyl chloride
3,17β-bis(toluene-4-sulfonyloxy)-1,3,5(10)-estratriene
Conditions | Yield |
---|---|
With pyridine; dmap for 2h; Ambient temperature; | 96.5% |
With pyridine | 87% |
Conditions | Yield |
---|---|
With pyridine at 20℃; | 96% |
With pyridine at 105 - 110℃; for 1h; | 80.03% |
With pyridine at 105 - 120℃; | |
With pyridine |
estradiol
C18H23BrO2
Conditions | Yield |
---|---|
With N-chloro-succinimide; sodium bromide In ethanol for 0.5h; Ambient temperature; | 96% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 20h; | 96% |
Stage #1: estradiol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide | 95% |
In N-methyl-acetamide | 95% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In methanol at 20℃; for 24h; Schlenk technique; | 96% |
With N-Bromosuccinimide In ethanol for 24h; | 55% |
Multi-step reaction with 2 steps 1.1: tetraethylammonium bromide / dimethylsulfoxide / Electrolysis 1.2: pyridine / CH2Cl2 2.1: KOH / methanol / 2 h / Heating View Scheme | |
With N-Bromosuccinimide In ethanol at 20℃; |
estradiol
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 96% |
With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 12h; Sealed tube; | 84% |
Stage #1: estradiol With triethylamine In acetonitrile at 20℃; for 0.166667h; Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h; Inert atmosphere; | 82% |
estradiol
Conditions | Yield |
---|---|
With Amberlyst A26-resin bound iodine azide In acetonitrile at 20℃; for 3h; Catalytic behavior; Inert atmosphere; | 96% |
estradiol
perfluorotoluene
3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>estra-1,3,5(10)-trien-17β-ol
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water for 1h; Ambient temperature; | 95% |
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.
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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