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50-28-2

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50-28-2 Usage

description

β-Estradiol is an endogenous estrogenic hormone receptor (ER) agonist (Ki values are 0.12 and 0.13 nM for ERα and ERβ respectively). Also high affinity ligand at membrane estrogen GPR30 receptors. β-Estradiol is an activator of PI 3-kinase.Estradiol (17β-estradiol, β-Estradiol, E2, 17β-Oestradiol) is a human sex hormone and steroid, and the primary female sex hormone. Estradiol upregulates IL-6 expression through the estrogen receptor β (ERβ) pathway.

Uses

Different sources of media describe the Uses of 50-28-2 differently. You can refer to the following data:
1. 17β-Estradiol is the major estrogen secreted by the premenopausal ovary.This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.β-Estradiol is used to study cell differentiation and transformations (tumorigenicity).
2. 17β-Estradiol is the major estrogen secreted by the premenopausal ovary.This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.
3. Estradiol is the major estrogen secreted by the premenopausal ovary.
4. Estradiol USP (Estrace) is used to treat Breast cancer; prostatic carcinoma.

Indications and Usage

Estradiol is a white or milky white ordorless crystalline powder. It is soluble in dioxane and acetone, slightly soluble in ethanol, and insoluble in water. Estradiol is the intermediate between estradiol valerate and estradiol benzoate, and it is a type of estrogen drug. It can be used to treat uterine functional bleeding, primary amenorrhea, menopausal syndrome, and prostate cancer. Estradiol can promote and adjust the normal growth of female sex organs and secondary sex characteristics, promote mammary duct maturation and growth, and aid in posseting. Estradiol can also be used in biochemical research.

Adverse reactions

In high dosages, estradiol can inhibit the release of anterior pituitary prolactin, thus decreasing breast milk secretion. However, nausea, vomiting and endometrial hyperplasia-induced bleeding may occur. Patients with liver or kidney failure should use with caution.

Contradictions

Do not use on breasts, vaginal area and vaginal mucosa.

Chemical Properties

Different sources of media describe the Chemical Properties of 50-28-2 differently. You can refer to the following data:
1. White or almost white, crystalline powder or colourless crystals.
2. Estradiol, 17-β-is an odorless white to yellow crystalline substance.

Application

β-Estradiol has been used:for the in vitro maturation of bovine cumulus-oocyte complexes (COCs)as a supplement in in vitro maturation medium (IVM), which is used as a control mediumin estrogen-induction assay

Definition

ChEBI: The 17beta-isomer of estradiol.

Acquired resistance

Estradiol is the most potent endogenous estrogen, exhibiting high affinity for the ER and high potency when administered parenterally. When administered orally, estradiol is promptly conjugated in the intestine and oxidatively metabolized by the liver, resulting in its low oral bioavailability and therapeutic effectiveness.

General Description

Estradiol, estra-1,3,5(10)-triene-3,17β-diol, is the most activeof the natural steroid estrogens. Although its 17β-OHgroup is vulnerable to bacterial and enzymatic oxidation toestrone, it can be temporarily protected as anester at C3 or C17, or permanently protected by adding a17α-alkyl group (e.g., 17α-ethinyl estradiol, the most commonlyused estrogen in oral contraceptives). The increasedoil solubility of the 17β-esters (relative to estradiol) permitsthe esters to remain in oil at the IM injection site for extendedperiods. These derivatives illustrate the principles of steroidmodification. Transdermal estradiolproducts avoid first-pass metabolism, allowing estradiol tobe as effective as oral estrogens for treating menopausalsymptoms. A new transdermal spray, Evamist, was approvedin 2007. Estradiol itself is typically not very effective orallybecause of rapid metabolism, but an oral formulation of micronizedestradiol that allows more rapid absorption of thedrug is available (Estrace). In addition to the oral and transdermalproducts, estradiol is also available in gel, cream, andvaginal ring formulations. The commercially available estradiolesters are the following:Estradiol 3-acetate, USP (oral; vaginal ring)Estradiol 17-valerate, USP (IM injection)Estradiol 17-cypionate, USP (IM injection).

Hazard

A carcinogen (OSHA).

Biological Activity

Endogenous estrogen receptor (ER) agonist (K i values are 0.12 and 0.13 nM for ER α and ER β respectively). Also high affinity ligand at membrane estrogen GPR30 receptors.

Contact allergens

Natural estradiol, used in transdermal systems for hormonal substitution, can induce allergic contact dermatitis, with the risk of systemic contact dermatitis after oral reintroduction.

Biochem/physiol Actions

The major estrogen secreted by the premenopausal ovary. Estrogens direct the development of the female phenotype in embryogenesis and during puberty by regulating gene transcription and, thus, protein synthesis. It also induces the production of gonadotropins which, in turn, induce ovulation. Exposure to estradiol increases breast cancer incidence and proliferation.

Mechanism of action

The most potent naturally occurring estrogen in mammals. It is synthesized primarily in the ovary, and also in the testis, adrenal gland and placenta, and to a limited extent by peripheral tissues (e.g., liver, fat, and skeletal muscle) from androstenedione and testosterone. It is responsible for the development of secondary sex characteristics in the female at puberty (i.e., growth and development of the vagina, uterus and fallopian tubes, enlargement of the breasts, and growth and maturation of long bones).

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. A promoter. Human reproductive effects by ingestion: ferthty effects. Experimental reproductive effects. Human mutation data reported. A steroid hormone much used in medicine. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

Estradiol, estra-1,3,5(10)-trien-3,17β-diol (28.1.17), is most easily made by reducing the keto-group of estrone by various reducing agents, in particular potassium borohydride.

Potential Exposure

The working environment may be contaminated during sex hormone manufacture, especially during the extraction and purification of natural steroid hormones; grinding of raw materials; handling of powdered products and recrystallization. Airborne particles of sex hormones may be absorbed through the skin, ingested or inhaled. Enteric absorption results in quick inactivation of sex hormones in the liver. The rate of inactivation is decreased for the oral, alkylated steroid hormones (methyl testosterone, anabolic steroids, etc.). Sex hormones may accumulate and reach relatively high levels even if their absorption is intermittent. Consequently, repeated absorption of small amounts may be detrimental to health. Intoxication by sex hormones may occur in almost all the exposed workers if preventive measures are not taken. The effect in the industrial sector is more successful than the agricultural one (chemical caponizing of cockerels by stilbestrol implants and incorporation of estrogens in feed for body weight gain promotion in beef cattle), where measures taken are summary and the number of cases of intoxication is consequently bigger

Shipping

UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials

Purification Methods

17-Estradiol (previously known as -estradiol) is purified by chromatography on SiO2 (toluene/EtOAc 4:1) and recrystallised from CHCl3/hexane or 80% EtOH. It is stable in air, is insoluble in H2O, and is precipitated by digitonin. The UV has max at 225 and 280 nm. The diacetate [3434-88-6] has m 97-98o and forms leaflets from aqueous EtOH. The 3-benzoate crystallises from aqueous MeOH withm 193o and [] D 25 +58o to 63o (c 1, dioxane). [Meischer & Scholz Helv Chim Acta 20 263, 1237 1937, Biochem J 32 1273 1938, Oppolzer & Roberts Helv Chim Acta 63 1703 1980, Inhoffen & Zühlsdorff Chem Ber 7 4 1914 1941, Beilstein 6 IV 6611.]

Check Digit Verification of cas no

The CAS Registry Mumber 50-28-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 50-28:
(4*5)+(3*0)+(2*2)+(1*8)=32
32 % 10 = 2
So 50-28-2 is a valid CAS Registry Number.
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+/m0/s1

50-28-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (E0025)  β-Estradiol  >97.0%(GC)

  • 50-28-2

  • 1g

  • 223.00CNY

  • Detail
  • TCI America

  • (E0025)  β-Estradiol  >97.0%(GC)

  • 50-28-2

  • 5g

  • 680.00CNY

  • Detail
  • TCI America

  • (E0025)  β-Estradiol  >97.0%(GC)

  • 50-28-2

  • 25g

  • 2,480.00CNY

  • Detail
  • Alfa Aesar

  • (L03801)  beta-Estradiol, 99% (dry wt.), ca 3% water   

  • 50-28-2

  • 1g

  • 383.0CNY

  • Detail
  • Alfa Aesar

  • (L03801)  beta-Estradiol, 99% (dry wt.), ca 3% water   

  • 50-28-2

  • 5g

  • 1492.0CNY

  • Detail
  • Alfa Aesar

  • (L03801)  beta-Estradiol, 99% (dry wt.), ca 3% water   

  • 50-28-2

  • 25g

  • 5984.0CNY

  • Detail
  • Sigma

  • (E8875)  β-Estradiol  ≥98%

  • 50-28-2

  • E8875-250MG

  • 600.21CNY

  • Detail
  • Sigma

  • (E8875)  β-Estradiol  ≥98%

  • 50-28-2

  • E8875-1G

  • 1,281.15CNY

  • Detail
  • Sigma

  • (E8875)  β-Estradiol  ≥98%

  • 50-28-2

  • E8875-5G

  • 4,450.68CNY

  • Detail
  • Sigma

  • (E8875)  β-Estradiol  ≥98%

  • 50-28-2

  • E8875-25G

  • 17,760.60CNY

  • Detail
  • Sigma

  • (E8875)  β-Estradiol  ≥98%

  • 50-28-2

  • E8875-100G

  • 37,486.80CNY

  • Detail

50-28-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 17β-estradiol

1.2 Other means of identification

Product number -
Other names 17-Beta-Estradiol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Veterinary Drug: PRODUCTION_AID
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:50-28-2 SDS

50-28-2Synthetic route

estrone acetate
901-93-9

estrone acetate

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
With diisobutylaluminium hydride; nickel dichloride In dichloromethane; toluene at -78℃; for 0.25h; Inert atmosphere;99%
3-O-methyl-17β-oestradiol
1035-77-4

3-O-methyl-17β-oestradiol

estradiol
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%
Estrone
53-16-7

Estrone

estradiol
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%
3-benzyloxyestra-1,3,5(10)-trien-17β-ol
14982-15-1

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

estradiol
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℃;
3,17β-bis(benzyloxy)estra-1,3,5(10)-triene
69455-04-5

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

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
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
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

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
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
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

estradiol
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%
methanol
67-56-1

methanol

17β-estradiol-3,17-disulfate potassium salt
17046-60-5

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

estradiol
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%
androsta-1,4-diene-3α/β,17β-diol
10520-93-1

androsta-1,4-diene-3α/β,17β-diol

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
With n-butyllithium In hexane; toluene at 100℃; for 11h; Aromatisation;83.8%
estradiol-17β 3-propargyl ether
28151-61-3

estradiol-17β 3-propargyl ether

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
With benzyltriethylammonium tetrathiomolybdate In acetonitrile at 28℃; for 48h;82%
(8R,9S,13S,14S,17S)-13-Methyl-3,17-bis-[1-(2-trimethylsilanyl-ethoxy)-ethoxy]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene

(8R,9S,13S,14S,17S)-13-Methyl-3,17-bis-[1-(2-trimethylsilanyl-ethoxy)-ethoxy]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 45℃; for 24h;81%
1β-hydroxy-3-trimethylsilylestra-1,3,5(10)-triene
250331-30-7

1β-hydroxy-3-trimethylsilylestra-1,3,5(10)-triene

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
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
1575722-51-8

(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
50-28-2

estradiol

Conditions
ConditionsYield
With proton-exchanged montmorillonite In dichloromethane at 20℃;78%
9(11)-Dehydroestradiol
791-69-5

9(11)-Dehydroestradiol

A

estradiol
50-28-2

estradiol

B

9beta-Estradiol
5864-38-0

9beta-Estradiol

Conditions
ConditionsYield
With Hexamethyldisiloxane; toluene-4-sulfonic acid In methanol; dichloromethane at -30 - 38℃;A 72.8%
B n/a
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

2,4-dibromo-3,17β-bis(trimethylsiloxy)estra-1,3,5(10)-triene
80128-36-5

2,4-dibromo-3,17β-bis(trimethylsiloxy)estra-1,3,5(10)-triene

A

estradiol
50-28-2

estradiol

B

2-(trimethylsilyl)estra-1,3,5(10)-triene-3,17β-diol
55934-99-1

2-(trimethylsilyl)estra-1,3,5(10)-triene-3,17β-diol

C

4-(trimethylsilyl)estra-1,3,5(10)-triene-3,17β-diol
55898-45-8

4-(trimethylsilyl)estra-1,3,5(10)-triene-3,17β-diol

Conditions
ConditionsYield
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
124-41-4

sodium methylate

3,17β-di-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>estra-1,3,5(10)-triene
90850-50-3

3,17β-di-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>estra-1,3,5(10)-triene

A

estradiol
50-28-2

estradiol

B

17β-<2,6-difluoro-3,5-dimethoxy-4-(trifluoromethyl)phenoxy>estra-1,3,5(10)-trien-3-ol
90850-54-7

17β-<2,6-difluoro-3,5-dimethoxy-4-(trifluoromethyl)phenoxy>estra-1,3,5(10)-trien-3-ol

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 10℃; for 2h;A 4%
B 68%
10β-Hydroxy-17β-(benzoyloxy)-19-norandrost-4-en-3-one
159045-76-8

10β-Hydroxy-17β-(benzoyloxy)-19-norandrost-4-en-3-one

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
With potassium hydroxide In methanol for 1h; Heating;68%
2-Iodoestradiol
24381-12-2

2-Iodoestradiol

A

estradiol
50-28-2

estradiol

B

2-Methoxyestradiol
362-07-2

2-Methoxyestradiol

Conditions
ConditionsYield
With copper(l) iodide; sodium methylate In methanol; N,N-dimethyl-formamideA 50%
B 3%
2-bromoestradiol
15833-07-5

2-bromoestradiol

sodium methylate
124-41-4

sodium methylate

A

estradiol
50-28-2

estradiol

B

2-Methoxyestradiol
362-07-2

2-Methoxyestradiol

Conditions
ConditionsYield
With copper(l) iodide In methanol; N,N-dimethyl-formamideA 50%
B 3%
2-bromoestradiol
15833-07-5

2-bromoestradiol

A

estradiol
50-28-2

estradiol

B

2-Methoxyestradiol
362-07-2

2-Methoxyestradiol

Conditions
ConditionsYield
With copper(l) iodide; sodium methylate In methanol; N,N-dimethyl-formamideA 50%
B 3%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

3-methoxy-17β-(trimethylsiloxy)estra-1,3,5(10)-triene
18880-67-6

3-methoxy-17β-(trimethylsiloxy)estra-1,3,5(10)-triene

A

estradiol
50-28-2

estradiol

B

D-1α-(trimethylsilyl)-17β-hydroxyestr-5(10)-en-3-one
76920-12-2

D-1α-(trimethylsilyl)-17β-hydroxyestr-5(10)-en-3-one

C

D-1α-(trimethylsilyl)-17β-hydroxyestr-4-en-3-one
86678-01-5

D-1α-(trimethylsilyl)-17β-hydroxyestr-4-en-3-one

D

(1R,8S,9S,13S,14S,17S)-17-Hydroxy-13-methyl-1-trimethylsilanyl-1,2,4,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

(1R,8S,9S,13S,14S,17S)-17-Hydroxy-13-methyl-1-trimethylsilanyl-1,2,4,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

Conditions
ConditionsYield
With 2O deg C; DME+HMPA; lithium; acetic acid Product distribution; oth. solvent;A 9.9%
B 37%
C 13%
D 9.9%
ethinyl estradiol
57-63-6

ethinyl estradiol

A

estradiol
50-28-2

estradiol

B

17α-vinylestradiol
7678-95-7

17α-vinylestradiol

Conditions
ConditionsYield
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%
estramustine
2998-57-4

estramustine

A

estradiol
50-28-2

estradiol

B

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
With cytosyl normal human prostate for 1h; Product distribution; Ambient temperature;A 9.6%
B 8.9%
6-dehydro-19-nortestosterone acetate
2590-41-2

6-dehydro-19-nortestosterone acetate

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

A

estradiol
50-28-2

estradiol

B

17β-acetoxy-7α-allyloestr-4-en-3-one
119020-33-6

17β-acetoxy-7α-allyloestr-4-en-3-one

Conditions
ConditionsYield
With diethylaluminium chloride In dichloromethane at -15℃; for 2.5h; Product distribution; other reagents and products; other solvents and temperatures;A 2%
B 2%
quinoline
91-22-5

quinoline

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
at 370 - 390℃;
at 370 - 390℃;
1,3,5-trinitrobenzene
99-35-4

1,3,5-trinitrobenzene

Estrone
53-16-7

Estrone

A

estradiol
50-28-2

estradiol

B

α-estradiol
57-91-0

α-estradiol

Conditions
ConditionsYield
With propan-1-ol; sodium
tetralin
119-64-2

tetralin

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
at 370 - 390℃;
at 370 - 390℃;
1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

estradiol
50-28-2

estradiol

Conditions
ConditionsYield
at 370 - 390℃;
at 370 - 390℃;
9,10-dihydrophenanthrene
776-35-2

9,10-dihydrophenanthrene

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

A

estradiol
50-28-2

estradiol

B

4-methyl-estratriene-(1.3.5(10))-diol-(1.17β)
3597-39-5

4-methyl-estratriene-(1.3.5(10))-diol-(1.17β)

Conditions
ConditionsYield
at 390℃;
Estrone
53-16-7

Estrone

A

estradiol
50-28-2

estradiol

B

Estriol
50-27-1

Estriol

Conditions
ConditionsYield
Isolierung aus dem Harn von Maennern nach Injektion von (+)-O-Acetyl-oestron;
estradiol
50-28-2

estradiol

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
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
110-87-2

3,4-dihydro-2H-pyran

estradiol
50-28-2

estradiol

3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene
3589-91-1

3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 3h;100%
With 2,4,6-Trinitrophenol In benzene98%
With toluene-4-sulfonic acid94%
estradiol
50-28-2

estradiol

diethyl dicarbonate
1609-47-8

diethyl dicarbonate

17β-Estradiol-bis-ethyl carbonate
105660-13-7

17β-Estradiol-bis-ethyl carbonate

Conditions
ConditionsYield
for 0.5h; Heating;100%
estradiol
50-28-2

estradiol

para-nitrophenyl triflate
17763-80-3

para-nitrophenyl triflate

3-(trifluoromethanesulfonyl)-β-estradiol
167845-80-9

3-(trifluoromethanesulfonyl)-β-estradiol

Conditions
ConditionsYield
With potassium carbonate In pentane for 2h; Ambient temperature;100%
estradiol
50-28-2

estradiol

Estrone
53-16-7

Estrone

Conditions
ConditionsYield
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%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

estradiol
50-28-2

estradiol

3-(t-butoxycarbonyl)-estradiol
1075685-75-4

3-(t-butoxycarbonyl)-estradiol

Conditions
ConditionsYield
With dmap In tetrahydrofuran; dichloromethane at -5 - 20℃; under 760.051 Torr; for 3h;100%
estradiol
50-28-2

estradiol

tert-butyl 2-(4-nitrophenyl)diazenecarboxylate
92722-14-0

tert-butyl 2-(4-nitrophenyl)diazenecarboxylate

C29H36N2O4
1262991-80-9

C29H36N2O4

Conditions
ConditionsYield
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%
vinyl acetate
108-05-4

vinyl acetate

estradiol
50-28-2

estradiol

estradiol 3-acetate
4245-41-4

estradiol 3-acetate

Conditions
ConditionsYield
With rubidium fluoride In acetonitrile at 80℃; for 1h;100%
estradiol
50-28-2

estradiol

<2,4-2H2>-1,3,5(10)-estratriene-3,17β-diol
53866-33-4

<2,4-2H2>-1,3,5(10)-estratriene-3,17β-diol

Conditions
ConditionsYield
With perchloric acid; chloroform-d1; d(4)-methanol at 75℃; for 144h; Inert atmosphere;100%
estradiol
50-28-2

estradiol

ethyl acetate
141-78-6

ethyl acetate

17-β-estradiol 17-acetate
1743-60-8

17-β-estradiol 17-acetate

Conditions
ConditionsYield
With C12F18O13Zn4 for 40h; Reflux; Inert atmosphere; chemoselective reaction;99%
With sodium hydrogen sulfate; silica gel In hexane at 67℃; for 72h;59%
estradiol
50-28-2

estradiol

N,N-Dimethylcarbamoyl chloride
79-44-7

N,N-Dimethylcarbamoyl chloride

3-O-[17β-hydroxy-estra-1,3,5(10)-trien]-yl-N,N-dimethylcarbamate

3-O-[17β-hydroxy-estra-1,3,5(10)-trien]-yl-N,N-dimethylcarbamate

Conditions
ConditionsYield
With potassium carbonate at 90℃; for 3h;98%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

estradiol
50-28-2

estradiol

3-(2-pyridoxy)estra-1,3,5(10)-trien-17β-ol

3-(2-pyridoxy)estra-1,3,5(10)-trien-17β-ol

Conditions
ConditionsYield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 90℃; for 24h;98%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

estradiol
50-28-2

estradiol

3,17β-bis(trimethylsiloxy)estra-1,3,5(10)-triene
5150-62-9

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

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexamethyl-disilazane In benzene for 5h; Heating;97%
estradiol
50-28-2

estradiol

benzyl bromide
100-39-0

benzyl bromide

3-benzyloxyestra-1,3,5(10)-trien-17β-ol
14982-15-1

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

Conditions
ConditionsYield
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
50-28-2

estradiol

chloromethyl methyl ether
107-30-2

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
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

Conditions
ConditionsYield
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%
estradiol
50-28-2

estradiol

methyl iodide
74-88-4

methyl iodide

3-O-methyl-17β-oestradiol
1035-77-4

3-O-methyl-17β-oestradiol

Conditions
ConditionsYield
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
50-28-2

estradiol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

3,17β-bis(toluene-4-sulfonyloxy)-1,3,5(10)-estratriene
144150-78-7

3,17β-bis(toluene-4-sulfonyloxy)-1,3,5(10)-estratriene

Conditions
ConditionsYield
With pyridine; dmap for 2h; Ambient temperature;96.5%
With pyridine87%
estradiol
50-28-2

estradiol

propionic acid anhydride
123-62-6

propionic acid anhydride

estradiol dipropionate
113-38-2

estradiol dipropionate

Conditions
ConditionsYield
With pyridine at 20℃;96%
With pyridine at 105 - 110℃; for 1h;80.03%
With pyridine at 105 - 120℃;
With pyridine
estradiol
50-28-2

estradiol

C18H23BrO2
79769-51-0

C18H23BrO2

Conditions
ConditionsYield
With N-chloro-succinimide; sodium bromide In ethanol for 0.5h; Ambient temperature;96%
estradiol
50-28-2

estradiol

benzyl bromide
100-39-0

benzyl bromide

3,17β-bis(benzyloxy)estra-1,3,5(10)-triene
69455-04-5

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

Conditions
ConditionsYield
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-acetamide95%
estradiol
50-28-2

estradiol

4-bromo-β-estradiol
1630-83-7

4-bromo-β-estradiol

Conditions
ConditionsYield
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
50-28-2

estradiol

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

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

Conditions
ConditionsYield
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
50-28-2

estradiol

(8S,9S,13S,14S,17S)-2,4,10-triazido-17-hydroxy-13-methyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro3H-cyclopenta[a]phenanthren-3-one

(8S,9S,13S,14S,17S)-2,4,10-triazido-17-hydroxy-13-methyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro3H-cyclopenta[a]phenanthren-3-one

Conditions
ConditionsYield
With Amberlyst A26-resin bound iodine azide In acetonitrile at 20℃; for 3h; Catalytic behavior; Inert atmosphere;96%
estradiol
50-28-2

estradiol

perfluorotoluene
434-64-0

perfluorotoluene

3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>estra-1,3,5(10)-trien-17β-ol
90850-46-7

3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>estra-1,3,5(10)-trien-17β-ol

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water for 1h; Ambient temperature;95%

50-28-2Relevant articles and documents

ANDROGEN METABOLISM IN MALE AND FEMALE BREAST TISSUE

Perel, E.,Davis, S.,Killinger, D. W.

, p. 345 - 352 (1981)

Incubation studies have been carried out using normal breast tissue and breast tissue from patients with gynecomastia, mammary dysplasia and breast carcinoma to determine the pattern of androstenedione metabolism.All tissues formed estrone (E1) and testosterone (T) in all incubations.Estradiol (E2) was isolated in incubations of tissue from 1 of 6 patients with mammary dysplasia, 5 of 6 patients with gynecomastia and in all incubations with normal and carcinoma tissue.Estrone formation was lowest in mammary dysplasia and gynecomastia, and higher in apparently normal breast tissue.The greatest E1 formation was found in incubations with breast carcinoma tissue, although there was considerable variation within this tissue group.Estradiol formation was low in all tissues, with the highest conversion rates in carcinoma tissue.Testosterone formation in carcinoma tissue was greater than in mammary dysplasia or gynecomastia, but similar to apparently normal tissue.These results indicate that breast tissue from different pathological states varies in its capacity to aromatize androstenedione (A) to estrogenic products and to convert it to other androgens.They have also shown that the pattern of metabolism is distinctive for the nature of the pathological abnormality.

Mechanism of action of bolandiol (19-nortestosterone-3β,17β-diol), a unique anabolic steroid with androgenic, estrogenic, and progestational activities

Attardi, Barbara J.,Page, Stephanie T.,Hild, Sheri A.,Coss, Christopher C.,Matsumoto, Alvin M.

, p. 151 - 161 (2010)

Bolandiol is a synthetic anabolic steroid that increases lean body mass and bone mineral density without significant stimulation of sex accessory glands in castrate adult male rats. Since bolandiol suppresses gonadotropins and endogenous testosterone (T) production, we investigated its mechanism of action. We compared the potency of bolandiol in vitro and in vivo with T, 5α-dihydrotestosterone (DHT), 19-nortestosterone (19-NT) and estradiol (E2). Bolandiol bound with lower affinity to the recombinant rat androgen receptor (AR) than the other androgens and had low, but measurable, affinity for recombinant human progestin receptors (PR-A, PR-B), and estrogen receptors (ERα and β-1). Functional agonist activity was assessed in transcription assays mediated by AR, PR, or ER. Bolandiol was stimulatory in all these assays, but only 4-9% as potent as T, DHT, and 19-NT via AR, 1% as potent as progesterone via PR, and 3% and 1% as potent as E2 acting through ERα or ERβ, respectively. In immature castrate rats, bolandiol was equipotent to T in stimulating growth of the levator ani muscle but less potent than T in stimulating growth of the sex accessory glands. Bolandiol also stimulated uterine weight increases in immature female rats, which were partly blocked by ICI 182,780, but it was not aromatized in vitro by recombinant human aromatase. In contrast to T, stimulation of sex accessory gland weights by bolandiol was not inhibited by concomitant treatment with the dual 5α-reductase inhibitor dutasteride. As bolandiol exhibits tissue selectivity in vivo, it may act via AR, PR, and/or ER, utilize alternative signaling pathway(s) or transcriptional coregulators, and/or be metabolized to a more potent selective steroid.

-

Whitman,Wintersteiner,Schwenk

, p. 789,794 (1937)

-

INHIBITION OF ESTROGEN SYNTHESIS IN HUMAN BREAST TUMORS BY TESTOLOLACTONE AND BROMOANDROSTENEDIONE

Budnick, Rose Marie,Dao, Thomas L.

, p. 533 - 542 (1980)

The inhibition of aromatase enzyme in human breast tumors by Δ1-testololactone, testololactone, 6α-bromoandrostenedione, and 6β-bromoandrostenedione was investigated.Estrone and estradiol synthesis from androstenedione was reduced in 3 tumor incubations by the presence of 0.13 mmol Δ1-testololactone and testololactone. 6α- and 6β-bromoandrostenedione (2.0 μM) were also shown to block estrogen synthesis in 2 tumors.Furthermore, Lineweaver-Burk plots revealed that all 4 compounds are competitive inhibitors of androstenedione aromatization.An apparent Km of the aromatase enzyme for androstenedione of 0.08 μM and a Vmax of 23 pmol of estrone synthesized/g tumor/hr were determined for one human breast tumor specimen.These results demonstrate that these aromatase inhibitors may be useful for the treatment of breast cancer.

Thermodynamic Meerwein-Ponndorf-Verley reduction in the diastereoselective synthesis of 17α-estradiol

Ahmed, Gulzar,Nickisch, Klaus

, p. 1 - 4 (2016)

The synthesis of 17α-hydroxy steroids generally requires multiple synthetic manipulations. The synthesis of 17α-estradiol is no exception, as this process involves the protection and release of the 3-hydroxy functional group. The diastereoselective reduction of the 17-keto-steroid can be utilized to prepare 17α-hydroxy-steroids. Here, 17α-estradiol was synthesized from commercially available estrone under thermodynamic Meerwein-Ponndorf-Verley (MPV) conditions in a single step, followed by simple chromatographic separation over silica gel. The remaining mixture of unreacted estrone and estradiols was easily recycled through Oppenauer oxidation to estrone, with an overall yield of 68% 17α-estradiol.

Estramustine binding in rat, baboon and human prostate measured by high pressure liquid chromatography

Kirdani,Corrales,Hoisaeter,Karr,Murphy,Sandberg

, p. 471 - 484 (1981)

High pressure liquid chromatography (HPLC) was used to determine 3H-estramustine (estradiol-17β3N-bis-[2-chlorethyl] carbamate), 3H-17β-hydroxy-5α-androstan-3-one (3H-dihydrotestosterone or 3H-DHT), 3H-estradiol-17β (3H-E2) and 3H-3β-hydroxy-5-pregnen-20-one (3H-pregnenolone) binding in 50μl of cytosol utilizing a column which separates proteins in the molecular weight range of 2,000 to 70,000 daltons. The rat prostate contains a protein in considerable concentration and with the highest affinity for estramustine (375,000dpm 3H-estramustine per mg. cytosol protein) among the substances tested. Operationally, we have named this protein 'estramustine binding protein' (EBP), though it is very likely similar to other previously described prostatic proteins (e.g., α-protein, prostatein, prostatic binding protein). The sensitivity of the HPLC method disclosed EBP-like proteins, but in much lesser concentrations, in some of the other tissues tested. The concentration of these proteins in the human and baboon prostates was much lower (average for the baboon cranial lobe 4800dpm/mg cytosol protein, with a somewhat higher value for the caudal lobe) than that in the rat gland. The amount of the EBP-like protein was higher in prostatic cancer than in that of benign prostatic hypertrophy (BPH) (range 9350 - 25,900 vs. 2200 - 18,900 dpm/mg cytosol protein). In the human, the highest value was found in one normal prostate tested (106,000 dpm/mg) cytosol protein).

An environmentally friendly and cost effective synthesis of estradiol featuring two novel reagents: Si(0)/KF and PMHS/hexamethyldisiloxane/pTSA

Lim, Chongsoo,Evenson, Gerald N.,Perrault, William R.,Pearlman, Bruce A.

, p. 6417 - 6420 (2006)

Si(0)/KF is introduced as a strong, inexpensive, environmentally friendly, and safe reagent for 'dissolving metal'-type reduction. PMHS/hexamethyldisiloxane/pTSA is introduced as an inexpensive substitute for Et3SiH/TFA for 'ionic hydrogenation', where the hexamethyldisiloxane functions as a capping agent to block the oligomeric silicone by-product from cross-linking to a gel, rubber, or plastic. An environmentally friendly and cost effective synthesis of estradiol is described which showcases these new reagents.

Catalytic properties of pristine and defect-engineered Zr-MOF-808 metal organic frameworks

Mautschke,Drache,Senkovska,Kaskel,Llabrés Xamena

, p. 3610 - 3616 (2018)

Various defect-engineered Zr-trimesate MOF-808 compounds (DE-MOF-808) have been prepared by mixing the tricarboxylate ligands with dicarboxylate ligands; viz. isophthalate, pyridine-3,5-dicarboxylate, 5-hydroxy-isophthalate, or 5-amino-isophthalate. The resulting mixed-ligand compounds, MOF-808-X (X = IP, Pydc, OH or NH2) were all found to be highly crystalline and isostructural to the unmodified MOF-808. Pristine MOF-808 showed better catalytic performance than a UiO-66 reference compound for the Meerwein-Ponndorf-Verley (MPV) reduction of carbonyl compounds. This was attributed to a higher availability of coordinatively unsaturated Zr4+ sites (cus) in MOF-808 upon removal of formate ions. Meanwhile, cus in UiO-66 are only located at defect sites and are thus much less abundant. Further improvement of the catalytic activity of defect-engineered MOF-808-IP and MOF-808-Pydc was observed, which may be related with the occurrence of less crowded Zr4+ sites in DE-MOF-808. The wider pore structure of MOF-808 with respect to UiO-66 compounds translates into a sharp improvement of the activity for the MPV reduction of bulky substrates, as shown for estrone reduction to estradiol. Interestingly, MOF-808 produces a notable diastereoselectivity towards the elusive 17-α-hydroxy estradiol.

Potent aromatase inhibitors through fungal transformation of anti-cancer drug testolactone: An approach towards treatment of breast cancer

-

Paragraph 0021, (2021/07/30)

Biotransformation of an aromatase inhibitor, testolactone (1), yielded five new metabolites, 7α-hydroxy-3-oxo-13,17-secoandrosta-1,4-dieno-17,13α-lactone (2), 7β-hydroxy-3-oxo-13,17-seco-5β-androsta-1-eno-17,13α-lactone (3), 3α,11β-dihydroxy-13,17-seco-5β-androsta-17,13α-lactone (4), 4β,5β-epoxy-3β-hydroxy-13,17-secoandrosta-1-eno-17,13α-lactone (5), and 4β,5β-epoxy-3α-hydroxy-13,17-secoandrosta-1-eno-17,13α-lactone (6). Aromatase (estrogen synthase) involves in the synthesis of estrogen, and promotes the growth of breast cancerous cells. It is a key target for the discovery of chemotherapeutic agents against ER+ (estrogen-positive) breast-cancers and several other diseases caused by overexpression of aromatase enzyme. Metabolites 3 (IC50=8.60±0.402 nM), and 4 (IC50=9.23±1.31 nM) were identified as potent inhibitors against human aromatase enzyme, in comparison to 1 (IC50=0.716±0.031 μM), and the standard aromatase inhibiting drug, exemestane (IC50=0.232±0.031 μM). Derivatives 2 (IC50=11.68±0.73 μM), 5 (IC50=10.37±0.50 μM) and 6 (IC50=0.82±0.059 μM) have also a good inhibition against aromatase enzyme. Therefore, metabolites 2-6 have the potential to serve as therapeutic agents against diseases caused by aromatase enzyme, including breast cancer.

Promiscuity of an unrelated anthrol reductase ofTalaromyces islandicusWF-38-12

Singh, Shailesh Kumar,Rajput, Anshul,De, Arijit,Chakraborti, Tapati,Husain, Syed Masood

, p. 474 - 478 (2021/02/09)

An anthrol reductase ofTalaromyces islandicusWF-38-12 (ARti-2) from an unrelated biosynthetic gene cluster (BGC) has been identified and characterized. It catalyses the NADPH-dependent reduction of anthrols (hydroanthraquinones), estrone and a naphthol with high stereo- and regioselectivity. The role of ARti-2, theCRG89872.1gene of the same BGC and non-enzymatic oxidation in the biosynthesis of (?)-flavoskyrin has been proposed.

Chiral Imidazo[1,5- a]pyridine-Oxazolines: A Versatile Family of NHC Ligands for the Highly Enantioselective Hydrosilylation of Ketones

Chinna Ayya Swamy,Varenikov, Andrii,Ruiter, Graham De

supporting information, p. 247 - 257 (2020/02/04)

Herein we report the synthesis and application of a versatile class of N-heterocyclic carbene ligands based on an imidazo[1,5-a]pyridine-3-ylidine backbone that is fused to a chiral oxazoline auxiliary. The key step in the synthesis of these ligands involves the installation of the oxazoline functionality via a microwave-assisted condensation of a cyano-azolium salt with a wide variety of 2-amino alcohols. The resulting chiral bidentate NHC-oxazoline ligands form stable complexes with rhodium(I) that are efficient catalysts for the enantioselective hydrosilylation of structurally diverse ketones. The corresponding secondary alcohols are isolated in good yields (typically >90%) with good to excellent enantioselectivities (80-93% ee). The reported hydrosilylation occurs at ambient temperatures (40 °C), with excellent functional group tolerability. Even ketones bearing heterocyclic substituents (e.g., pyridine or thiophene) or complex organic architectures are hydrosilylated efficiently, which is discussed further in this report.

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